# Patent

## Title
As-indacen derivatives

## Abstract

The present invention relates to compounds of the formula I




where

    X1, X2, R1, R2, A1, A2, Z1, Z2, m, n and rings B and B′ are as defined in claim 1.

## Background
The present invention relates to as-indacene derivatives, to liquid-crystalline media comprising these derivatives, and to electro-optical display elements containing these liquid-crystalline media. In particular, the invention relates to as-indacene derivatives of negative dielectric anisotropy.
Liquid crystals have found widespread use since the first commercially usable liquid-crystalline compounds were found about 30 years ago. Known areas of application are, in particular, displays for watches and pocket calculators, and large display panels as used in railway stations, airports and sports arenas. Further areas of application are displays of portable computers and navigation systems and video applications. For the last-mentioned applications in particular, high demands are made of the response times and contrast of the images.
The spatial arrangement of the molecules in a liquid crystal has the effect that many of its properties are direction-dependent. Of particular importance for use in liquid-crystal displays are the optical, dielectric and elasto-mechanical anisotropies. Depending on whether the molecules are oriented with their longitudinal axes perpendicular or parallel to the two plates of a capacitor, the latter has a different capacitance; in other words, the dielectric constant ε of the liquid-crystalline medium has different values for the two orientations. Substances whose dielectric constant is greater when the longitudinal axes of the molecules are oriented perpendicular to the capacitor plates than when they are oriented parallel are referred to as dielectrically positive. In other words, if the dielectric constant ε∥ parallel to the longitudinal axes of the molecules is greater than the dielectric constant ε⊥ perpendicular to the longitudinal axes of the molecules, the dielectric anisotropy Δε=ε∥−ε⊥ is greater than zero. Most liquid crystals used in conventional displays fall into this group.
Both the polarisability of the molecule and the permanent dipole moment play a role for the dielectric anisotropy. On application of a voltage to the display, the longitudinal axis of the molecules orients itself in such a way that the larger of the dielectric constants becomes effective. The strength of the interaction with the electric field depends on the difference between the two constants. In the case of small differences, higher switching voltages are necessary than in the case of large differences. The introduction of suitable polar groups, such as, for example, nitrile groups or fluorine, into the liquid-crystal molecules enables a broad range of working voltages to be achieved.
In the case of the liquid-crystalline molecules used in conventional liquid-crystal displays, the dipole moment oriented along the longitudinal axis of the molecules is larger than the dipole moment oriented perpendicular to the longitudinal axis of the molecules. In the most widespread TN (“twisted nematic”) cells, a liquid-crystalline layer with a thickness of only from about 5 to 10 μm is arranged between two plane-parallel glass plates, onto each of which an electrically conductive, transparent layer of tin oxide or indium tin oxide (ITO) has been vapour-deposited as electrode. A likewise transparent alignment layer, usually consisting of a plastic (for example polyimides), is located between these films and the liquid-crystalline layer. This alignment layer serves to bring the longitudinal axes of the adjacent liquid-crystalline molecules into a preferential direction through surface forces in such a way that, in the voltage-free state, they lie uniformly with the same orientation, flat or with the same small tilt angle, on the inside of the display surface. Two polarisation films which only enable linear-polarised light to enter and escape are applied to the outside of the display in a certain arrangement.
By means of liquid crystals in which the larger dipole moment is oriented parallel to the longitudinal axis of the molecule, very high-performance displays have already been developed. In most cases here, mixtures of from 5 to 20 components are used in order to achieve a sufficiently broad temperature range of the mesophase and short response times and low threshold voltages. However, difficulties are still caused by the strong viewing-angle dependence in liquid-crystal displays as are used, for example, for laptops. The best imaging quality can be achieved if the surface of the display is perpendicular to the viewing direction of the observer.
If the display is tilted relative to the observation direction, the imaging quality deteriorates drastically under certain circumstances. For greater comfort, attempts are being made to maximise the angle through which the display can be tilted from the viewing direction of an observer without significantly reducing the imaging quality. Attempts have recently been made to improve the viewing-angle dependence using liquid-crystalline compounds whose dipole moment perpendicular to the longitudinal axis of the molecule is larger than that parallel to the longitudinal axis of the molecule. The dielectric anisotropy Δε is negative. In the field-free state, these molecules are oriented with their longitudinal axes perpendicular to the glass surface of the display. Application of an electric field causes them to orient themselves more or less parallel to the glass surfaces. By achieving a plurality of domains, it has been possible to achieve an improvement in the viewing-angle dependence using liquid-crystalline media of negative dielectric anisotropy. This technology can also be used to achieve shorter response times in displays and better contrast values. Displays of this type are known as VA-TFT (“vertically aligned”) displays.
Development in the area of liquid-crystalline materials is still far from complete. In order to improve the properties of liquid-crystalline display elements, attempts are constantly being made to develop novel compounds which enable optimisation of such displays.
DE 25 14 389 A discloses, inter alia, 7-substituted 6-oxo-6H-indeno[5,4-b]furancarboxylic acids and the use thereof as medicaments; neither mesogenic properties nor the use of these compounds in liquid-crystalline media are described.
J. Heterocycl. Chem., 15 (1978) 43-48, discloses 2,7-dimethylbenzo[1,2-b:4,3-b′]difuran and 4-chloro-2,7-dimethylbenzo[1,2-b:4,3-b′]difuran; neither mesogenic properties nor the use of these compounds in liquid-crystalline media are described.
EP 1 350 780 A1 describes in general 1,7-dihydroindacene derivatives of negative dielectric anisotropy, without the physical or electro-optical properties being specified in detail.
An object of the present invention is to provide compounds having advantageous properties for use in liquid-crystalline media. In particular, they should have negative dielectric anisotropy, which makes them particularly suitable for use in liquid-crystalline media for VA displays.
This object is achieved in accordance with the invention by compounds of the general formula I




in which:





independently of one another, stand for





    A1 and A2 each, independently of one another, denote 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
    Z1 and Z2 each, independently of one another, denote a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
    R1 and R2 denote hydrogen, an alkanyl, alkoxy, alkenyl or alkynyl radical having 1 to 15 or 2 to 15 C atoms respectively, each of which is unsubstituted, monosubstituted by —CN or —CF3 or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF5;
    m and n, independently of one another, are 0, 1, 2 or 3;
    X1, X2 and Y2 each, independently of one another, denote hydrogen, an alkanyl, alkoxy, alkenyl or alkynyl radical having 1 to 15 or 2 to 15 C atoms respectively, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS;
    Y1 is as defined for Y2 or stands for —[—Z3-A3-]p-R3, where Z3 is as defined for Z1 and Z2, A3 is as defined for A1 and A2, R3 is as defined for R1 and R2, and p is as defined for n and m;

where

    A1, A2, A3, Z1, Z2, Z3, R1, R2 and R3 may each have identical or different meanings if m, n and p respectively are greater than 1;
    Y1 and Y2 may each have identical or different meanings for rings B and B′;

and where

    (a) R1 does not stand for —COOH if ring B stands for ring f or g and ring B′ stands for ring d and at the same time m is zero and X2 is not H, or R2 does not stand for —COOH if ring B′ stands for ring f or g and ring B stands for ring d and n is zero and X1 is not H;
    (b) R1-[-A1-Z1—]m— and —[—Z2-A2-]-R2 are not simultaneously CH3 if one of X1 and X2 is hydrogen and the other of X1 and X2 is hydrogen or Cl and at the same time both rings B and B′ stand for ring g.


The compounds have negative Δε and are therefore suitable, in particular, for use in VA-TFT displays. The compounds according to the invention preferably have a Δε of <−2 and particularly preferably a Δε of <−5. They exhibit very good compatibility with the usual substances used in liquid-crystal mixtures for displays.
Furthermore, the compounds of the formula I according to the invention have values for the optical anisotropy Δn which are particularly suitable for use in VA-TFT displays. The compounds according to the invention preferably have a Δn of greater than 0.02 and less than 0.25.
The other physical, physicochemical or electro-optical parameters of the compounds according to the invention are also advantageous for use of the compounds in liquid-crystalline media. The compounds have, in particular, a sufficient breadth of the nematic phase and good low-temperature and long-term stability as well as sufficiently high clearing points and good viscosities and response times.
It is preferred for at least one of the radicals X1 and X2 on the central aromatic six-membered ring of the compound of the formula I to be other than hydrogen.
It is furthermore preferred for at least one of rings B and B′ to have at least one electronegative radical (for example —F, —Cl or ═O or halogen-substituted alkyl radicals). It is particularly preferred for both rings B and B′ to have electronegative radicals.
The radicals X1 and X2, preferably —CF3, —OCF3, fluorine and/or chlorine substituents, in particular fluorine substituents, on the central aromatic six-membered ring and the preferably electronegative radicals on ring B or B′ produce a dipole moment perpendicular to the longitudinal axis of the molecule, which can optionally be further strengthened by suitable substituents in the wing units —(Z1-A1-)m-R1 and —(Z2-A2-)n-R2. In the field-free state, the compounds of the formula I orient themselves with their longitudinal molecular axis perpendicular to the treated or coated glass surface of the display.
Preferred compounds of the formula I according to the invention are those in which rings B and B′ are each, independently of one another, selected from




where Y1 and Y2 are as defined above for the formula I. It is particularly preferred here for rings B and B′ to be identical, where the radical Y1 in the two rings may have identical or different meanings and the radical Y2 in the two rings may have identical or different meanings.

Y1 and Y2 are particularly preferably, independently of one another, F, Cl or a (per)fluorinated alkanyl or alkoxy radical having up to 6 carbon atoms, in particular —CF3 or —OCF3. Furthermore, Y1 is particularly preferably also —[—Z3-A3-]p-R3. Y1 and Y2 in at least one of the rings B and B′ are very particularly preferably F, in particular in both rings.
It is furthermore preferred for the compounds of the formula I according to the invention to be selected from the group consisting of compounds of the following formulae:







where

    X1, X2, R1, R2, A1, A2, Z1, Z2, m and n are as defined in claim 1 and as defined above for the formula I;
    Y11 and Y12 are as defined for Y1 in claim 1 and as defined above for the formula I and can have identical or different meanings; and
    Y21 and Y22 are as defined for Y2 in claim 1 and as defined above for the formula I and can have identical or different meanings.


Y11, Y12, Y21 and Y22 are particularly preferably, independently of one another, H, F, Cl or a (per)fluorinated alkanyl or alkoxy radical having up to 6 carbon atoms, in particular —CF3 or —OCF3. Furthermore, Y11 and Y12 particularly preferably also stand for —[—Z3-A3-]p-R3. Y11 and Y21 or Y12 and Y22 are very particularly preferably identical and are in particular fluorine. In particular, Y11, Y21, Y12 and Y22 are all simultaneously fluorine.
Particular preference is given to compounds of the formulae Iaa, Ibb, Iee, Iff and Igg.
In the compounds of the general formula I and of the formulae Iaa, Iaf, Iag, Ibb, Ibf, Ibg, Icc, Idd, Iee, Iff and Igg according to the invention, Z1 and Z2 and—if present—Z3 preferably, independently of one another, stand for a single bond, —CF2O—, —OCF2—, —CF2CF2—, —CH═CH—, —CF═CH—, —CH═CF— or —CF═CF—, particularly preferably a single bond, —CF2O— or —OCF2—, in particular a single bond.
In the compounds of the formula I and of the formulae Iaa, Iaf, Iag, Ibb, Ibf, Ibg, Icc, Idd, Iee, Iff and Igg according to the invention, A1, A2 and—if present—A3 are preferably, independently of one another, optionally substituted 1,4-phenylene, optionally substituted 1,4-cyclohexylene, in which —CH2— may be replaced once or twice by —O—, or optionally substituted 1,4-cyclohexenylene. In the case where m>1, the rings A1 may adopt identical or different meanings. In the case where n>1, the rings A2 may adopt identical or different meanings. In the case where p>1, the rings A3 may adopt identical or different meanings.
A1, A2 and—if present—A3 are particularly preferably, independently of one another,




A1, A2 and—if present—A3 are very particularly preferably 1,4-cyclohexylene rings and/or optionally fluorine-substituted 1,4-phenylene rings.
R1, R2, R3, X1, X2, Y1 and Y2 in the formula I may each, independently of one another, be an alkanyl radical and/or an alkoxy radical (alkyloxy radical) having 1 to 15 C atoms which is straight-chain or branched. It is preferably straight-chain, has 1, 2, 3, 4, 5, 6 or 7 C atoms and is accordingly preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy.
R1, R2, R3, X1, X2, Y1 and Y2 in the formula I may each, independently of one another, be oxaalkyl—i.e. one of the non-terminal CH2 groups of the alkanyl radical has been replaced by —O——preferably straight-chain 2-oxapropyl (=methoxymethyl), 2-(=ethoxymethyl) or 3-oxabutyl (=methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, or 2-, 3-, 4-, 5- or 6-oxaheptyl. In a corresponding manner, R1, R2, R3, X1, X2, Y1, and Y2 in the formula I may also, independently of one another, be thioalkanyl or sulfonylalkanyl radicals, i.e. alkanyl radicals in which one CH2 group has been replaced by —S— or —SO2—.
R1, R2, R3, X1, X2, Y1 and Y2 in the formula I may furthermore each, independently of one another, be an alkenyl radical having 2 to 15 C atoms which is straight-chain or branched and has at least one C—C double bond. It is preferably straight-chain and has 2 to 7 C atoms. Accordingly, it is preferably vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or 4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, or hept-1-, -2-, -3-, 4-, -5- or -6-enyl. If the two C atoms of the C—C double bond are substituted, the alkenyl radical can be in the form of the E and/or Z isomer (trans/cis). In general, the respective E isomers are preferred.
R1, R2, R3, X1, X2, Y1 and Y2 in the formula I may also, independently of one another, be an alkynyl radical having 2 to 15 C atoms which is straight-chain or branched and has at least one C—C triple bond.
R1, R2, R3, X1, X2, Y1 and Y2 in the formula I may each, independently of one another, be an alkanyl radical having 1 to 15 C atoms in which one CH2 group has been replaced by —O— and one has been replaced by —CO—, these preferably being adjacent. This thus contains an acyloxy group —CO—O— or an oxycarbonyl group —O—CO—. This radical is preferably straight-chain and has 2 to 6 C atoms. The following of these radicals are preferred here: acetoxy, propionyloxy, butyryloxy, pentanoyloxy, hexanoyloxy, acetoxymethyl, propionyloxymethyl, butyryloxymethyl, pentanoyloxymethyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-acetoxypropyl, 3-propionyloxypropyl, 4-acetoxybutyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, butoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 3-(ethoxycarbonyl)propyl and 4-(methoxycarbonyl)butyl. Furthermore, an alkanyl radical can also have an —O—CO—O— unit. Replacement of a CH2 group by only one —CO— group (carbonyl function) is also possible.
R1, R2, R3, X1, X2, Y1 and Y2 in the formula I may each, independently of one another, be an alkenyl radical having 2 to 15 C atoms in which a CH2 group in the vicinity of an unsubstituted or substituted —C═C— unit has been replaced by —CO— or —CO—O— or —O—CO—, where this radical may be straight-chain or branched. The radical is preferably straight-chain and has 4 to 13 C atoms. Particular preference is given here to acryloyloxymethyl, 2-acryloyloxyethyl, 3-acryloyloxypropyl, 4-acryloyloxybutyl, 5-acryloyloxypentyl, 6-acryloyloxyhexyl, 7-acryloyloxyheptyl, 8-acryloyloxyoctyl, 9-acryloyloxynonyl, methacryloyloxymethyl, 2-methacryloyloxyethyl, 3-methacryloyloxypropyl, 4-methacryloyloxybutyl, 5-methacryloyloxypentyl, 6-methacryloyloxyhexyl, 7-methacryloyloxyheptyl and 8-methacryloyloxyoctyl. Correspondingly, a CH2 group in the vicinity of a substituted —C≡C-unit in an alkynyl radical may also be replaced by —CO—, —CO—O—, —O—CO— or —O—CO—O—.
R1, R2 and R3 in the formula I may each, independently of one another, be an alkanyl radical having 1 to 15 C atoms or alkenyl radical having 2 to 15 C atoms which is monosubstituted by —CN or —CF3, where these are preferably straight-chain. The substitution by —CN or —CF3 is possible in any desired position.
R1, R2, R3, X1, X2, Y1 and Y2 in the formula I may each, independently of one another, be an alkanyl radical in which two or more CH2 groups have been replaced by —O— and/or —CO—O—, where this may be straight-chain or branched. It is preferably branched and has 3 to 12 C atoms.
R1, R2, R3, X1, X2, Y1 and Y2 in the formula I may each, independently of one another, be an alkanyl radical having 1 to 15 C atoms or an alkenyl radical having 2 to 15 C atoms which is monosubstituted or polysubstituted by F, Cl, Br and/or I, where these radicals are preferably straight-chain and halogen is preferably —F and/or —Cl. In the case of polysubstitution, halogen is preferably —F. The resultant radicals also include perfluorinated radicals, such as —CF3. In the case of monosubstitution, the fluorine or chlorine substituent can be in any desired position, but is preferably in the ω position.
R1, R2, R3, X1, X2, Y1 and Y2 in the formula I may also each, independently of one another, be —F, —Cl, —Br, —I, —CN, —SCN, —NCS or —SF5.
R1, R2 and R3 in the general formula I are particularly preferably, independently of one another, an alkanyl radical, alkoxy radical or alkenyl radical having 1 to 7 or 2 to 7 C atoms respectively.
X1 and X2 in the general formula I are preferably, independently of one another, hydrogen, an alkanyl radical, alkoxy radical or alkenyl radical having 1 to 7 or 2 to 7 C atoms respectively, each of which is at least monosubstituted by halogen, or a halogen. It is particularly preferred here for at least one of X1 and X2 to be —CF3, —OCF3, F or Cl. Very particularly preferably, both radicals X1 and X2 are —CF3, —OCF3, fluorine or chlorine, and in particular both are fluorine.
Preferred compounds of the general formula I have a total of zero, one, two or three wing units —Z1-A1- and —Z2-A2-, i.e. n+m=0, 1, 2 or 3, where n and m are each 0, 1, 2 or 3. If two or three wing units are present, they may be bonded to only one side of the molecule, i.e. to ring B or to ring B′, or alternatively to both sides of the molecule. Particularly preferably, n+m=0 or 1.
In connection with the present invention, halogen denotes fluorine, chlorine, bromine and iodine.
In connection with the present invention, the term “alkyl”—unless defined otherwise elsewhere in this description or in the claims—denotes a straight-chain or branched aliphatic hydrocarbon radical having 1 to 15 (i.e. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15) carbon atoms; this radical is unsubstituted or monosubstituted or polysubstituted by fluorine, chlorine, bromine, iodine, carboxyl, nitro, —NH2, —N(alkanyl)2 and/or cyano, where the polysubstitution can take place with identical or different substituents. If this alkyl radical is a saturated radical, it is also referred to as “alkanyl”. Furthermore, the term “alkyl” also encompasses hydrocarbon radicals which are unsubstituted or correspondingly mono- or polysubstituted by identical or different substituents, in particular by F, Cl, Br, I and/or —CN, and in which one or more CH2 groups may be replaced by —O— (“alkoxy”, “oxaalkyl”), —S— (“thioalkyl”), —SO2—, —CH═CH— (“alkenyl”), —C≡C— (“alkynyl”), —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that hetero atoms (O or S) in the chain are not linked directly to one another. Alkyl is preferably a straight-chain or branched, unsubstituted or substituted alkanyl, alkenyl or alkoxy radical having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms.
Since one or more CH2 groups in an alkyl radical may be replaced by —O—, the term “alkyl” also encompasses “alkoxy” or “oxaalkyl” radicals. In connection with the present invention—if the term is not defined otherwise elsewhere in the description or in the claims—the term alkoxy is taken to mean an O-alkyl radical in which the oxygen atom is bonded directly to the alkoxy-substituted group or the substituted ring and alkyl is as defined above; alkyl is preferably then alkanyl or alkenyl. Preferred alkoxy radicals are methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy and octoxy, where each of these radicals may also be substituted, preferably by one or more fluorine atoms. Alkoxy is particularly preferably —OCH3, —OC2H5, —O-n-C3H7, —O-n-C4H9, —O-t-C4H9, —OCF3, —OCHF2, —OCHF or —OCHFCHF2. In connection with the present invention, the term “oxaalkyl”—if the term is not defined otherwise elsewhere in the description or in the claims—denotes alkyl radicals in which at least one non-terminal CH2 group has been replaced by —O— in such a way that there are no adjacent hetero atoms (O or S). Oxaalkyl preferably encompasses straight-chain radicals having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.
In connection with the present invention, the term “alkenyl”—unless defined otherwise in the claims or elsewhere in this description—denotes an alkyl radical as defined above in which one or more —CH═CH— groups are present. If two —CH═CH— groups are present in the radical, this may also be referred to as “alkadienyl”. An alkenyl radical can contain 2 to 15 (i.e. 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15) carbon atoms and is branched or preferably straight-chain. The radical is unsubstituted or mono- or polysubstituted by identical or different substituents, in particular by F, Cl, Br, I and/or CN. Furthermore, one or more CH2 groups may each, independently of one another, be replaced by —O—, —S—, —C≡C—, —CO—, —CO—O—, —O—CO—, —O—CO—O— in such a way that hetero atoms (O or S) are not bonded directly to one another. If the CH═CH group carries a radical other than hydrogen on both carbon atoms, for example if it is a non-terminal group, the CH═CH group can exist in two configurations, namely as the E isomer and as the Z isomer. In general, the E isomer (trans) is preferred. The alkenyl radical preferably contains 2, 3, 4, 5, 6 or 7 carbon atoms and denotes vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, 2-propenyl, 2E-butenyl, 2E-pentenyl, 2E-hexenyl, 2E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl or 6-heptenyl.
If one or more CH2 groups in an alkyl radical have been replaced by —C≡C—, an alkynyl radical is present. Replacement of one or more CH2 groups by —CO—O— or —O—CO— is also possible. The following of these radicals are preferred here: acetoxy, propionyloxy, butyryloxy, pentanoyloxy, hexanoyloxy, acetoxymethyl, propionyloxymethyl, butyryloxymethyl, pentanoyloxymethyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-acetoxypropyl, 3-propionyloxypropyl, 4-acetoxybutyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, butoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 3-(ethoxycarbonyl)propyl and 4-(methoxycarbonyl)butyl.
If one CH2 group in an alkyl radical has been replaced by unsubstituted or substituted —CH═CH— and an adjacent CH2 group has been replaced by CO, CO—O or O—CO, this radical may be straight-chain or branched. It is preferably straight-chain and has 4 to 12 C atoms. Accordingly, it particularly preferably denotes acryloyloxymethyl, 2-acryloyloxyethyl, 3-acryloyloxypropyl, 4-acryloyloxybutyl, 5-acryloyloxypentyl, 6-acryloyloxyhexyl, 7-acryloyloxyheptyl, 8-acryloyloxyoctyl, 9-acryloyloxynonyl, methacryloyloxymethyl, 2-methacryloyloxyethyl, 3-methacryloyloxypropyl, 4-methacryloyloxybutyl, 5-methacryloyloxypentyl, 6-methacryloyloxyhexyl, 7-methacryloyloxyheptyl or 8-methacryloyloxyoctyl.
If radicals or substituents of the compounds according to the invention or the compounds according to the invention themselves can exist as optically active or stereoisomeric radicals, substituents or compounds respectively since they have, for example, a centre of asymmetry, these are also encompassed by the present invention. It goes without saying here that the compounds of the general formula I according to the invention can exist in isomerically pure form, for example as pure enantiomers, diastereomers, E or Z isomers, trans or cis isomers, or as a mixture of a plurality of isomers in any desired ratio, for example as a racemate, E/Z isomer mixture or cis/trans isomer mixture.
The compounds of the general formula I are prepared by methods known per se, as described in the literature (for example in the standard works, such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart), to be precise under reaction conditions which are known and suitable for the said reactions. Use can be made here of variants which are known per se, but are not mentioned here in greater detail.
If desired, the starting materials can also be formed in situ by not isolating them from the reaction mixture, but instead immediately converting them further into the compounds of the general formula I.
The syntheses of various polysubstituted phenyl derivatives which are used to build up the as-indacene derivatives according to the invention containing the fused five-membered rings B and B′ are described by way of example in the examples. The starting substances are obtainable by generally accessible literature procedures or are commercially available. The reactions described should likewise be regarded as known from the literature.
An illustrative synthesis for building up the as-indacene skeleton is shown below. The synthesis can be adapted to the particular desired compounds of the general formula I through the choice of suitable starting materials.




Starting from the 1,2-dibromophenol derivative A, reaction with the α,β-unsaturated aldehyde B1 in the presence of lithium diisopropylamide (LDA) gives compound C. Repetition of this reaction with the aldehyde B gives D. D reacts with palladium catalysis in the presence of triethylamine with ring closure to give the diketone E (=compound Icc). The diketone E and 1,2-ethanedithiol in the presence of BF3/diethyl ether give the corresponding bisdithiane F. This is reacted with 1,3-dibromo-5,5-dimethylhydantoin (DBH) and HF in pyridine to give G. Elimination of HBr in the presence of diazabicycloundecene (DBU) gives the as-indacene derivative H (=compound Ibb where Y11═Y12═Y21═Y22═F). The as-indacene derivative H is hydrogenated on palladium/carbon catalyst in a hydrogen atmosphere to give the as-indacene derivative J (=compound Iaa where Y11═Y12═Y21═Y22═F).




On the one hand, reduction of the diketone E, for example using LiAlH4, gives the alcohol K, from which on the one hand subsequent elimination using acid gives the as-indacene derivative L (=compound lee where Y11═Y21═H) and on the other hand using DAST (diaminosulfur trifluoride; cf. M. Hudlicky, Organic Reactions, 35, 1988, 513) gives the as-indacene derivative M (=compound Iaa where Y11═Y12═F and Y21═Y22═H) analogously to the process described in DE 44 34 975 A1.




Furthermore, reaction of the diketone E with DAST analogously to the process disclosed in DE 44 34 975 A1 gives the as-indacene derivative N (=compound lee where Y1═Y2═F).
The introduction of chlorine atoms (instead of fluorine atoms) is also possible starting from the diketone E with phosphoryl chloride with warming in dimethylformamide. Trifluoromethyl radicals are introduced analogously to the process disclosed in DE 10135499 A1 starting from the diketone E.
A further illustrative synthesis of compounds of the formula I according to the invention is shown by the following scheme:




Starting from O, a trimethylsilyl group can be introduced into the phenyl ring using n-butyllithium and trimethylsilyl chloride; subsequent reaction with the acid chloride shown with Lewis acid catalysis gives P. Depending on the meaning of the radical —[—Z3-A3-]p-R3, it is introduced with formation of Q by a Wittig reaction and subsequent catalytic hydrogenation (p=0, R3=alkyl) or by reaction with a suitable organometallic compound containing —[—Z3-A3-]p-R3 as structural unit, subsequent elimination of the OH group formed and final catalytic reduction. Cyclisation to give R is carried out after saponification of the ester function and conversion into an acid chloride with Lewis acid catalysis. The resultant keto function of R can be reduced by means of a Wolff-Kishner reduction, followed by silylation using trimethylsilyl chloride and reaction with the acid chloride shown to give S. Cyclisation to give T is carried out with acid catalysis. Starting from T, further compounds of the formula I according to the invention are then accessible in the manner described above.
Compounds according to the invention containing one or two oxygen-containing five-membered rings can be prepared in accordance with the following scheme or with adaptation thereof and of the syntheses described for the formation of the carbocyclic five-membered rings:




After diazotisation and introduction of the second OH group using iodine/potassium carbonate, the aromatic compound U is converted into the diiodinated aromatic compound V. With catalysis using bistriphenylphosphinepalladium(II) chloride and copper(I) iodide, the alkyne R1-[-A1-Z1—]m≡ or R2-[-A2-Z2—]n-≡ gives the benzodifuran W, from which X is also accessible by means of catalytic hydrogenation.
The following synthesis sequence illustrates the preparation of compounds according to the invention having an oxygen-containing five-membered ring, where recourse can be made to the preparation methods explained for the above schemes for the individual synthesis steps.




The reactions described should only be regarded as illustrative. The person skilled in the art can carry out corresponding variations of the syntheses described and also follow other suitable synthetic routes in order to obtain compounds of the formula I.
As already mentioned, the compounds of the general formula I can be used in liquid-crystalline media.
The present invention therefore also relates to a liquid-crystalline medium comprising at least two liquid-crystalline compounds, comprising at least one compound of the general formula I.
The present invention also relates to liquid-crystalline media comprising 2 to 40, preferably 4 to 30, components as further constituents besides one or more compounds of the formula I according to the invention. These media particularly preferably comprise 7 to 25 components besides one or more compounds according to the invention. These further constituents are preferably selected from nematic or nematogenic (monotropic or isotropic) substances, in particular substances from the classes of the azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, 1,3-dioxanes, 2,5-tetrahydropyrans, phenyl or cyclohexyl benzoates, phenyl or cyclohexyl esters of cyclohexanecarboxylic acid, phenyl or cyclohexyl esters of cyclohexylbenzoic acid, phenyl or cyclohexyl esters of cyclohexylcyclohexanecarboxylic acid, cyclohexylphenyl esters of benzoic acid, of cyclohexanecarboxylic acid or of cyclohexylcyclohexanecarboxylic acid, phenylcyclohexanes, cyclohexylbiphenyls, phenylcyclohexylcyclohexanes, cyclohexylcyclohexanes, cyclohexylcyclohexylcyclohexenes, 1,4-biscyclohexylbenzenes, 4′,4′-biscyclohexylbiphenyls, phenyl- or cyclohexylpyrimidines, phenyl- or cyclohexylpyridines, phenyl- or cyclohexyldioxanes, phenyl- or cyclohexyl-1,3-dithianes, 1,2-diphenylethanes, 1,2-dicyclohexylethanes, 1-phenyl-2-cyclohexylethanes, 1-cyclohexyl-2-(4-phenylcyclohexyl)ethanes, 1-cyclohexyl-2-biphenylethanes, 1-phenyl-2-cyclohexylphenylethanes, optionally halogenated stilbenes, benzyl phenyl ethers, tolans and substituted cinnamic acids. The 1,4-phenylene groups in these compounds may also be mono- or polyfluorinated.
The most important compounds suitable as further constituents of media according to the invention can be characterised by the formulae (II), (III), (IV), (V) and (VI):

R′-L-E-R′′  (II)

R′-L-COO-E-R′′  (III)

R′-L-OOC-E-R′′  (IV)

R′-L-CH2CH2-E-R′′  (V)

R′-L-CF2O-E-R′′  (VI)

In the formulae (II), (III), (IV), (V) and (VI), L and E, which may be identical or different, each, independently of one another, denote a divalent radical from the group formed by -Phe-, -Cyc-, -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -Pyr-, -Dio-, -Thp-, -G-Phe- and -G-Cyc- and their mirror images, where Phe denotes unsubstituted or fluorine-substituted 1,4-phenylene, Cyc denotes trans-1,4-cyclohexylene or 1,4-cyclohexylene, Pyr denotes pyrimidine-2,5-diyl or pyridine-2,5-diyl, Dio denotes 1,3-dioxane-2,5-diyl,
Thp denotes tetrahydropyran-2,5-diyl and G denotes 2-(trans-1,4-cyclohexyl)ethyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl.
One of the radicals L and E is preferably Cyc or Phe. E is preferably Cyc, Phe or Phe-Cyc. The media according to the invention preferably comprise one or more components selected from the compounds of the formulae (II), (III), (IV), (V) and (VI) in which L and E are selected from the group consisting of Cyc and Phe and simultaneously one or more components selected from the compounds of the formulae (II), (III), (IV), (V) and (VI) in which one of the radicals L and E is selected from the group consisting of Cyc and Phe and the other radical is selected from the group consisting of -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -G-Phe- and -G-Cyc-, and optionally one or more components selected from the compounds of the formulae (II), (III), (IV), (V) and (VI) in which the radicals L and E are selected from the group consisting of -Phe-Cyc-, -Cyc-Cyc-, -G-Phe- and -G-Cyc-.
In a smaller sub-group of the compounds of the formulae (II), (III), (IV), (V) and (VI), R′ and R′′ each, independently of one another, denote alkyl, alkenyl, alkoxy, alkoxyalkyl (oxaalkyl), alkenyloxy or alkanoyloxy having up to 8 C atoms. This smaller sub-group is called group A below, and the compounds are referred to by the sub-formulae (IIa), (IIIa), (IVa), (Va) and (VIa). In most of these compounds, R′ and R′′ are different from one another, one of these radicals usually being alkyl, alkenyl, alkoxy or alkoxyalkyl (oxaalkyl).
In another smaller sub-group of the compounds of the formulae (II), (III), (IV), (V) and (VI), which is known as group B, E denotes




In the compounds of group B, which are referred to by the sub-formulae (IIb), (IIIb), (IVb), (Vb) and (VIb), R′ and R′′ have the meaning indicated for the compounds of the sub-formulae (IIa) to (VIa) and are preferably alkyl, alkenyl, alkoxy or alkoxyalkyl (oxaalkyl).
In a further smaller sub-group of the compounds of the formulae (II), (III), (IV), (V) and (VI), R′′ denotes —CN. This sub-group is referred to below as group C, and the compounds of this sub-group are correspondingly described by the sub-formulae (IIc), (IIIc), (IVc), (Vc) and (VIc). In the compounds of the sub-formulae (IIc), (IIIc), (IVc), (Vc) and (VIc), R′ has the meaning indicated for the compounds of the sub-formulae (IIa) to (VIa) and is preferably alkyl, alkenyl, alkoxy or alkoxyalkyl (oxaalkyl).
Besides the preferred compounds of groups A, B and C, other compounds of the formulae (II), (III), (IV), (V) and (VI) having other variants of the proposed substituents are also customary. All these substances are obtainable by methods which are known from the literature or analogously thereto.
Besides the compounds of the general formula I according to the invention, the media according to the invention preferably comprise one or more compounds from groups A, B and/or C. The proportions by weight of the compounds from these groups in the media according to the invention are:

    group A: 0 to 90%, preferably 20 to 90%, in particular 30 to 90%
    group B: 0 to 80%, preferably 10 to 80%, in particular 10 to 70%
    group C: 0 to 80%, preferably 5 to 80%, in particular 5 to 50%.


The media according to the invention preferably comprise 1 to 40%, particularly preferably 5 to 30%, of the compounds of the formula I according to the invention. Preference is furthermore given to media comprising more than 40%, in particular 45 to 90%, of compounds of the formula I according to the invention. The media preferably comprise one, two, three, four or five compounds of the formula I according to the invention.
Examples of the compounds of the formulae (II), (III), (IV), (V) and (VI) are the compounds listed below:







where Ra and Rb, independently of one another, are —CnH2n+1 or —OCnH2n+1, and n=1, 2, 3, 4, 5, 6, 7 or 8, and L1 and L2, independently of one another, are —H or —F,








where m and n, independently of one another, are 1, 2, 3, 4, 5, 6, 7 or 8.

The media according to the invention are prepared in a manner conventional per se. In general, the components are dissolved in one another, advantageously at elevated temperature. By means of suitable additives, the liquid-crystalline phases of the present invention can be modified in such a way that they can be used in all types of liquid-crystal display element that have been disclosed hitherto. Additives of this type are known to the person skilled in the art and are described in detail in the literature (H. Kelker/R. Hatz, Handbook of Liquid Crystals, Verlag Chemie, Weinheim, 1980). For example, pleochroic dyes can be used for the production of coloured guest-host systems or substances can be added in order to modify the dielectric anisotropy, the viscosity and/or the alignment of the nematic phases.
Owing to their negative Δε, the compounds of the formula I are particularly suitable for use in VA-TFT displays.
The present invention therefore also relates to electro-optical liquid-crystal display elements containing a liquid-crystalline medium according to the invention.
The invention is explained in greater detail below with reference to working examples, but without being restricted thereby.


EXAMPLES
The starting substances can be obtained by generally accessible literature procedures or are commercially available. The reactions described are known from the literature.
Physical, physicochemical or electro-optical parameters are determined by generally known methods, as described, inter alia, in the brochure “Merck Liquid Crystals—Licristal®—Physical Properties of Liquid Crystals—Description of the Measurement Methods”, 1998, Merck KGaA, Darmstadt.
Example A




At −75° C., a solution of 13.5 g (50.0 mmol) of 1,2-dibromo-4,5-difluorobenzene 2 in 10 ml of THF is added to 27.0 ml of a solution, diluted with 100 ml, of 2N lithium diisopropylamide (LDA) in cyclohexane/ethylbenzene/THF (54.0 mmol). After 2 hours at the low temperature, 4.6 g (47.0 mmol) of the aldehyde 1 in 10 ml of THF are added. After 30 minutes, the cooling is removed, and 100 ml of 1N HCl are added to the batch at 20° C. Extraction of the aqueous phase, drying of the organic phase, evaporation and chromatography gives the allyl alcohol 3. Repetition of this reaction starting from 3 gives the bisallyl alcohol 4.




35.0 g (74.8 mmol) of the bisallyl alcohol 4, 5.5 g of bis(tri-o-tolylphosphine)palladium dichloride and 50 ml of triethylamine are dissolved in 390 ml of acetonitrile and warmed at 90° C. until the allyl alcohol has reacted completely. The cooled batch is introduced into water. Extraction, drying, evaporation and chromatography gives the diketone 5.
Example B




10.0 g (32.6 mmol) of the diketone 5 and 7.0 ml (69.9 mmol) of propane-dithiol are dissolved in 50 ml of dichloromethane, and 7.0 ml of boron trifluoride/diethyl ether complex are added at 6 to 7° C., and the mixture is subsequently stirred overnight at room temperature. The batch is added to 10 ml of saturated sodium hydrogencarbonate solution, and the mixture is stirred until the evolution of gas is complete. After extraction of the aqueous phase, drying of the organic phase, evaporation and filtration through silica gel, the residue obtained is employed in the next step without further purification.




10.0 g of the crude thioketal 6, dissolved in 30 ml of dichloromethane, are slowly added at −75° C. to a mixture of 45.8 g (160 mmol) of 1,3-dibromo-5,5-dimethylhydantoin (DBH), 80 ml of a 65% solution of hydrogen fluoride in pyridine and 50 ml of dichloromethane. The batch is subsequently stirred overnight at room temperature. The reaction mixture is added to ice-cooled hydrogen sulfite solution and deacidified using saturated sodium hydrogencarbonate solution and sodium hydroxide solution. Extraction, drying, evaporation, re-washing with water, chromatography and crystallisation from hexane gives the as-indacene derivative 7.




6.0 g (11.8 mmol) of the as-indacene derivative 7 are dissolved in 50 ml of dichloromethane, 4.5 ml (30.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are added, and the mixture is stirred at room temperature until the starting material has reacted completely. The batch is washed with water and saturated sodium chloride solution, evaporated and chromatographed, and the as-indacene derivative 8 is isolated.
Example C




4.0 g (11.6 mmol) of the as-indacene derivative 8 are dissolved in 50 ml of THF and hydrogenated at room temperature and atmospheric pressure on a palladium catalyst. Evaporation, chromatography on silica gel and crystallisation gives the as-indacene derivative 9.
Example D




Under nitrogen, 116.5 g (1.00 mol) of 1,2-difluorobenzene (10) are dissolved in 600 ml of tetrahydrofuran, and 656 ml of a 15% solution of butyllithium in n-hexane (1.05 mol) are added at −70° C. After 1 h at this temperature, a solution of 132.6 ml (1.05 mol) of trimethylsilyl chloride (11) in 100 ml of tetrahydrofuran is slowly added to the reaction mixture. The batch thaws overnight and is added to 1.5 l of sat. ammonium chloride solution. The organic phase is dried over sodium sulfate and evaporated: the residue obtained is distilled at 8 mbar, giving 152 g (81%, b.p. 88° C.) of the silyl compound 12.




Under nitrogen, 37.6 g (250 mmol) of the acid chloride 13 are dissolved in 200 ml of cyclohexane. 46.6 g (250 mmol) of the silyl compound 12 are added to the solution at 0-2° C. 37.3 g (280 mmol) of aluminum chloride are subsequently added in portions to the reaction mixture, during which the temperature is held between −2° C. and 2° C. After 1 h at low temperature, the cooling is removed. The batch warms to room temperature and is transferred onto ice. The aqueous phase is extracted with methyl tert-butyl ether, and the organic phase is dried over sodium sulfate and evaporated. The residue is purified on silica gel, giving 31.4 g (55%) of the keto ester 14.




Under nitrogen, 51.1 g (150 mmol) of the Wittig salt 15 are suspended in 200 ml of THF, and a solution of 15.7 g (140 mmol) of potassium tertbutoxide in 75 ml of THF is added at 5-10° C. After one hour, the keto ester 14 dissolved in 75 ml of THF is added. The cooling is subsequently removed. After 20 h at room temp., water is added to the batch. The aqueous phase is extracted with MTB ether. The organic phase is washed with sat. sodium chloride solution, dried over sodium sulfate and evaporated. The residue is passed through silica gel (MTB ether/n-hexane 1:10), giving 29.4 g (88%) of the ester 16.




29.0 g (21.6 mmol) of the ester 16 are dissolved in 500 ml of tetrahydrofuran and hydrogenated on a palladium catalyst. The hydrogenation solution is evaporated, and the residue is chromatographed on silica gel, giving 27.8 g (95%) of substance 17.




27.0 g (105 mmol) of the ester 17 are refluxed for 5 h in ethanolic potassium hydroxide solution. The alcohol is subsequently distilled off, and the residue is taken up in water, acidified using hydrochloric acid and extracted with MTB ether. The organic phase is dried over sodium sulfate and evaporated. 50 ml of thionyl chloride and one drop of DMF are added to the residue obtained, and the mixture is refluxed until the evolution of gas is complete. Excess thionyl chloride is distilled off. The residue (25 g) is employed in the next step without further purification.




A solution of 25 g (about 105 mmol) of the crude acid chloride 18 in 120 ml of dichloromethane is added under nitrogen and at −20 to −15° C. to a suspension of 16.4 g (119 mmol) of aluminium chloride in 80 ml of dichloromethane. After 4.5 h, the reaction is terminated by addition of ice, and the mixture is acidified using hydrochloric acid. The aqueous phase is extracted with methylene chloride. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on silica gel (MTB/n-heptane 1:5), giving 18.5 g (84%) of the indanone 19.




23.9 g (361 mmol) of potassium hydroxide are dissolved in 90 ml of diethylene glycol. 13.0 ml (268 mmol) of hydrazinium hydroxide and 18.0 g (85.6 mmol) of the indanone 19 are added to the solution, and the mixture is refluxed for 2 h. The temperature of the heating bath is subsequently raised to 200° C. and maintained until the evolution of gas is complete. The cooled reaction mixture is poured into water and acidified. The aqueous phase is extracted with n-pentane. The organic phase is dried over sodium sulfate and evaporated. The residue is purified by chromatography on silica gel (n-pentane), giving 11.4 g (68%) of the indane 20.




The silylation of the indane 20 is carried out in accordance with the above procedure. The purification is carried out by chromatography on silica gel (n-pentane). 11.0 g (56.5 mmol) of the indane 20 give 12.6 g (84%) of the silyl compound 21.




The acylation of the silyl compound 21 is carried out in accordance with the above procedure. 12.0 g (44.7 mmol) of 21 give 6.8 g (52%) of the ketone 23.




6.5 g (22.2 mmol) of the ketone 23 are introduced into 30 l of trifluoromethanesulfonic acid with ice cooling and stirring. After 24 h, the batch is transferred onto ice and extracted with MTB ether. The organic phase is washed with sat. sodium hydrogencarbonate solution, dried over sodium sulfate and evaporated. The residue is purified on silica gel (MTB ether/n-heptane 1:8), giving 2.6 g (40%) of the indacene 24.
The further derivatisation of 24 is carried out analogously to Examples B and C.
Example E




25.0 g (172 mmol) of the aromatic compound 1 are dissolved in 10 ml of semi-conc. hydrochloric acid, and 11.9 g (172 mmol) of sodium nitrite in 70 ml of water are added at a temperature of below 5° C. When the addition of nitrite is complete, the batch is diluted with 100 ml of water and heated to the boil. When the evolution of nitrogen has subsided (bubble counter), the batch is refluxed for a further hour. The cooled reaction solution is extracted with MTB ether. The organic phase is dried over sodium sulfate and evaporated, giving 13.7 g (54%) of the diol 26.




13.0 g (90.0 mmol) of the phenol 26 and 48 g (348 mmol) of potassium carbonate are dissolved in 160 ml of water, and 50 g (200 mmol) of iodine are added in portions at 5° C. The batch is stirred overnight. The reaction solution is decanted off from the resultant precipitate and acidified using hydrochloric acid. The aqueous phase is extracted with MTB ether, washed with sat. sodium chloride solution, dried over sodium sulfate and evaporated. The residue is passed through silica gel (MTB ether/heptane 2:1), giving 20.1 g (57%) of the diiodinated aromatic compound 27.




Under nitrogen, 20.0 g (50.3 mmol) of the phenol 27 are dissolved in 120 ml of dimethylformamide and 28 ml of triethylamine, and 1.0 g of bistriphenylphosphinepalladium(II) chloride and 580 mg of copper(I) iodide are added. A solution of 10.3 ml (105 mmol) of 1-pentyne in 30 ml of dimethylformamide is subsequently added slowly to the batch. The batch is stirred at room temp. until the conversion is complete (TLC). Water is added to the reaction mixture, which is extracted with MTB ether. The organic phase is dried over sodium sulfate and evaporated. Chromatography on silica gel gives 6.5 g (46%) of the benzodifuran 28.




6.0 g (21.6 mmol) of the benzodifuran 28 are dissolved in 100 ml of tetrahydrofuran and hydrogenated on a palladium catalyst. The hydrogenation solution is evaporated, and the residue is chromatographed on silica gel, giving 5.5 g (90%) of substance 29.
The following compounds were prepared in accordance with or analogously to Examples A to E. “bond” here stands for a single bond:
Examples 1-259




Examples 260-518




Examples 519-777
















 













Example No.
X1
X2
R1
R2







 1, 260, 519,
H
H
H
CH3



 2, 261, 520,
H
H
H
C2H5



 3, 262, 521,
H
H
H
n-C3H7



 4, 263, 522,
H
H
H
n-C4H9



 5, 264, 523,
H
H
H
n-C5H11



 6, 265, 524,
H
H
H
n-C6H13



 7, 266, 525,
H
H
H
n-C7H15



 8, 267, 526,
F
H
H
CH3



 9, 268, 527,
F
H
H
C2H5



 10, 269, 528,
F
H
H
n-C3H7



 11, 270, 529,
F
H
H
n-C4H9



 12, 271, 530,
F
H
H
n-C5H11



 13, 272, 531,
F
H
H
n-C6H13



 14, 273, 532,
F
H
H
n-C7H15



 15, 274, 533,
H
F
H
CH3



 16, 275, 534,
H
F
H
C2H5



 17, 276, 535,
H
F
H
n-C3H7



 18, 277, 536,
H
F
H
n-C4H9



 19, 278, 537,
H
F
H
n-C5H11



 20, 279, 538,
H
F
H
n-C6H13



 21, 280, 539,
H
F
H
n-C7H15



 22, 281, 540,
F
F
H
CH3



 23, 282, 541,
F
F
H
C2H5



 24, 283, 542,
F
F
H
n-C3H7



 25, 284, 543,
F
F
H
n-C4H9



 26, 285, 544,
F
F
H
n-C5H11



 27, 286, 545,
F
F
H
n-C6H13



 28, 287, 546,
F
F
H
n-C7H15



 29, 288, 547,
CF3
H
H
CH3



 30, 289, 548,
CF3
H
H
C2H5



 31, 290, 549,
CF3
H
H
n-C3H7



 32, 291, 550,
CF3
H
H
n-C4H9



 33, 292, 551,
CF3
H
H
n-C5H11



 34, 293, 552,
CF3
H
H
n-C6H13



 35, 294, 553,
CF3
H
H
n-C7H15



 36, 295, 554,
H
CF3
H
CH3



 37, 296, 555,
H
CF3
H
C2H5



 38, 297, 556,
H
CF3
H
n-C3H7



 39, 298, 557,
H
CF3
H
n-C4H9



 40, 299, 558,
H
CF3
H
n-C5H11



 41, 300, 559,
H
CF3
H
n-C6H13



 42, 301, 560,
H
CF3
H
n-C7H15



 43, 302, 561,
—OCF3
H
H
CH3



 44, 303, 562,
—OCF3
H
H
C2H5



 45, 304, 563,
—OCF3
H
H
n-C3H7



 46, 305, 564,
—OCF3
H
H
n-C4H9



 47, 306, 565,
—OCF3
H
H
n-C5H11



 48, 307, 566,
—OCF3
H
H
n-C6H13



 49, 308, 567,
—OCF3
H
H
n-C7H15



 50, 309, 568,
H
—OCF3
H
CH3



 51, 310, 569,
H
—OCF3
H
C2H5



 52, 311, 570,
H
—OCF3
H
n-C3H7



 53, 312, 571,
H
—OCF3
H
n-C4H9



 54, 313, 572,
H
—OCF3
H
n-C5H11



 55, 314, 573,
H
—OCF3
H
n-C6H13



 56, 315, 574,
H
—OCF3
H
n-C7H15



 57, 316, 575,
H
H
CH3
CH3



 58, 317, 576,
H
H
CH3
C2H5



 59, 318, 577,
H
H
CH3
n-C3H7



 60, 319, 578,
H
H
CH3
n-C4H9



 61, 320, 579,
H
H
CH3
n-C5H11



 62, 321, 580,
H
H
CH3
n-C6H13



 63, 322, 581,
H
H
CH3
n-C7H15



 64, 323, 582,
F
H
CH3
CH3



 65, 324, 583,
F
H
CH3
C2H5



 66, 325, 584,
F
H
CH3
n-C3H7



 67, 326, 585,
F
H
CH3
n-C4H9



 68, 327, 586,
F
H
CH3
n-C5H11



 69, 328, 587,
F
H
CH3
n-C6H13



 70, 329, 588,
F
H
CH3
n-C7H15



 71, 330, 589,
F
F
CH3
CH3



 72, 331, 590,
F
F
CH3
C2H5



 73, 332, 591,
F
F
CH3
n-C3H7



 74, 333, 592,
F
F
CH3
n-C4H9



 75, 334, 593,
F
F
CH3
n-C5H11



 76, 335, 594,
F
F
CH3
n-C6H13



 77, 336, 595,
F
F
CH3
n-C7H15



 78, 337, 596,
CF3
H
CH3
CH3



 79, 338, 597,
CF3
H
CH3
C2H5



 80, 339, 598,
CF3
H
CH3
n-C3H7



 81, 340, 599,
CF3
H
CH3
n-C4H9



 82, 341, 600,
CF3
H
CH3
n-C5H11



 83, 342, 601,
CF3
H
CH3
n-C6H13



 84, 343, 602,
CF3
H
CH3
n-C7H15



 85, 344, 603,
—OCF3
H
CH3
CH3



 86, 345, 604,
—OCF3
H
CH3
C2H5



 87, 346, 605,
—OCF3
H
CH3
n-C3H7



 88, 347, 606,
—OCF3
H
CH3
n-C4H9



 89, 348, 607,
—OCF3
H
CH3
n-C5H11



 90, 349, 608,
—OCF3
H
CH3
n-C6H13



 91, 350, 609,
—OCF3
H
CH3
n-C7H15



 92, 351, 610,
H
H
C2H5
C2H5



 93, 352, 611,
H
H
C2H5
n-C3H7



 94, 353, 612,
H
H
C2H5
n-C4H9



 95, 354, 613,
H
H
C2H5
n-C5H11



 96, 355, 614,
H
H
C2H5
n-C6H13



 97, 356, 615,
H
H
C2H5
n-C7H15



 98, 357, 616,
F
H
C2H5
CH3



 99, 358, 617,
F
H
C2H5
C2H5



100, 359, 618,
F
H
C2H5
n-C3H7



101, 360, 619,
F
H
C2H5
n-C4H9



102, 361, 620,
F
H
C2H5
n-C5H11



103, 362, 621,
F
H
C2H5
n-C6H13



104, 363, 622,
F
H
C2H5
n-C7H15



105, 364, 623,
F
F
C2H5
C2H5



106, 365, 624,
F
F
C2H5
n-C3H7



107, 366, 625,
F
F
C2H5
n-C4H9



108, 367, 626,
F
F
C2H5
n-C5H11



109, 368, 627,
F
F
C2H5
n-C6H13



110, 369, 628,
F
F
C2H5
n-C7H15



111, 370, 629,
CF3
H
C2H5
CH3



112, 371, 630,
CF3
H
C2H5
C2H5



113, 372, 631,
CF3
H
C2H5
n-C3H7



114, 373, 632,
CF3
H
C2H5
n-C4H9



115, 374, 633,
CF3
H
C2H5
n-C5H11



116, 375, 634,
CF3
H
C2H5
n-C6H13



117, 376, 635,
CF3
H
C2H5
n-C7H15



118, 377, 636,
—OCF3
H
C2H5
CH3



119, 378, 637,
—OCF3
H
C2H5
C2H5



120, 379, 638,
—OCF3
H
C2H5
n-C3H7



121, 380, 639,
—OCF3
H
C2H5
n-C4H9



122, 381, 640,
—OCF3
H
C2H5
n-C5H11



123, 382, 641,
—OCF3
H
C2H5
n-C6H13



124, 383, 642,
—OCF3
H
C2H5
n-C7H15



125, 384, 643,
H
H
n-C3H7
n-C3H7



126, 385, 644,
H
H
n-C3H7
n-C4H9



127, 386, 645,
H
H
n-C3H7
n-C5H11



128, 387, 646,
H
H
n-C3H7
n-C6H13



129, 388, 647,
H
H
n-C3H7
n-C7H15



130, 389, 648,
F
H
n-C3H7
CH3



131, 390, 649,
F
H
n-C3H7
C2H5



132, 391, 650,
F
H
n-C3H7
n-C3H7



133, 392, 651,
F
H
n-C3H7
n-C4H9



134, 393, 652,
F
H
n-C3H7
n-C5H11



135, 394, 653,
F
H
n-C3H7
n-C6H13



136, 395, 654,
F
H
n-C3H7
n-C7H15



137, 396, 655,
F
F
n-C3H7
n-C3H7



138, 397, 656,
F
F
n-C3H7
n-C4H9



139, 398, 657,
F
F
n-C3H7
n-C5H11



140, 399, 658,
F
F
n-C3H7
n-C6H13



141, 400, 659,
F
F
n-C3H7
n-C7H15



142, 401, 660,
CF3
H
n-C3H7
CH3



143, 402, 661,
CF3
H
n-C3H7
C2H5



144, 403, 662,
CF3
H
n-C3H7
n-C3H7



145, 404, 663,
CF3
H
n-C3H7
n-C4H9



146, 405, 664,
CF3
H
n-C3H7
n-C5H11



147, 406, 665,
CF3
H
n-C3H7
n-C6H13



148, 407, 666,
CF3
H
n-C3H7
n-C7H15



149, 408, 667,
—OCF3
H
n-C3H7
CH3



150, 409, 668,
—OCF3
H
n-C3H7
C2H5



151, 410, 669,
—OCF3
H
n-C3H7
n-C3H7



152, 411, 670,
—OCF3
H
n-C3H7
n-C4H9



153, 412, 671,
—OCF3
H
n-C3H7
n-C5H11



154, 413, 672,
—OCF3
H
n-C3H7
n-C6H13



155, 414, 673,
—OCF3
H
n-C3H7
n-C7H15



156, 415, 674,
H
H
n-C4H9
n-C4H9



157, 416, 675,
H
H
n-C4H9
n-C5H11



158, 417, 676,
H
H
n-C4H9
n-C6H13



159, 418, 677,
H
H
n-C4H9
n-C7H15



160, 419, 678,
F
H
n-C4H9
CH3



161, 420, 679,
F
H
n-C4H9
C2H5



162, 421, 680,
F
H
n-C4H9
n-C3H7



163, 422, 681,
F
H
n-C4H9
n-C4H9



164, 423, 682,
F
H
n-C4H9
n-C5H11



165, 424, 683,
F
H
n-C4H9
n-C6H13



166, 425, 684,
F
H
n-C4H9
n-C7H15



167, 426, 685,
F
F
n-C4H9
n-C4H9



168, 427, 686,
F
F
n-C4H9
n-C5H11



169, 428, 687,
F
F
n-C4H9
n-C6H13



170, 429, 688,
F
F
n-C4H9
n-C7H15



171, 430, 689,
CF3
H
n-C4H9
CH3



172, 431, 690,
CF3
H
n-C4H9
C2H5



173, 432, 691,
CF3
H
n-C4H9
n-C3H7



174, 433, 692,
CF3
H
n-C4H9
n-C4H9



175, 434, 693,
CF3
H
n-C4H9
n-C5H11



176, 435, 694,
CF3
H
n-C4H9
n-C6H13



177, 436, 695,
CF3
H
n-C4H9
n-C7H15



178, 437, 696,
—OCF3
H
n-C4H9
CH3



179, 438, 697,
—OCF3
H
n-C4H9
C2H5



180, 439, 698,
—OCF3
H
n-C4H9
n-C3H7



181, 440, 699,
—OCF3
H
n-C4H9
n-C4H9



182, 441, 700,
—OCF3
H
n-C4H9
n-C5H11



183, 442, 701,
—OCF3
H
n-C4H9
n-C6H13



184, 443, 702,
—OCF3
H
n-C4H9
n-C7H15



185, 444, 703,
H
H
n-C5H11
n-C5H11



186, 445, 704,
H
H
n-C5H11
n-C6H13



187, 446, 705,
H
H
n-C5H11
n-C7H15



188, 447, 706,
F
H
n-C5H11
CH3



189, 448, 707,
F
H
n-C5H11
C2H5



190, 449, 708,
F
H
n-C5H11
n-C3H7



191, 450, 709,
F
H
n-C5H11
n-C4H9



192, 451, 710,
F
H
n-C5H11
n-C5H11



193, 452, 711,
F
H
n-C5H11
n-C6H13



194, 453, 712,
F
H
n-C5H11
n-C7H15



195, 454, 713,
F
F
n-C5H11
n-C5H11



196, 455, 714,
F
F
n-C5H11
n-C6H13



197, 456, 715,
F
F
n-C5H11
n-C7H15



198, 457, 716,
CF3
H
n-C5H11
CH3



199, 458, 717,
CF3
H
n-C5H11
C2H5



200, 459, 718,
CF3
H
n-C5H11
n-C3H7



201, 460, 719,
CF3
H
n-C5H11
n-C4H9



202, 461, 720,
CF3
H
n-C5H11
n-C5H11



203, 462, 721,
CF3
H
n-C5H11
n-C6H13



204, 463, 722,
CF3
H
n-C5H11
n-C7H15



205, 464, 723,
—OCF3
H
n-C5H11
CH3



206, 465, 724,
—OCF3
H
n-C5H11
C2H5



207, 466, 725,
—OCF3
H
n-C5H11
n-C3H7



208, 467, 726,
—OCF3
H
n-C5H11
n-C4H9



209, 468, 727,
—OCF3
H
n-C5H11
n-C5H11



210, 469, 728,
—OCF3
H
n-C5H11
n-C6H13



211, 470, 729,
—OCF3
H
n-C5H11
n-C7H15



212, 471, 730,
H
H
n-C6H13
n-C6H13



213, 472, 731,
H
H
n-C6H13
n-C7H15



214, 473, 732,
F
H
n-C6H13
CH3



215, 474, 733,
F
H
n-C6H13
C2H5



216, 475, 734,
F
H
n-C6H13
n-C3H7



217, 476, 735,
F
H
n-C6H13
n-C4H9



218, 477, 736,
F
H
n-C6H13
n-C5H11



219, 478, 737,
F
H
n-C6H13
n-C6H13



220, 479, 738,
F
H
n-C6H13
n-C7H15



221, 480, 739,
F
F
n-C6H13
n-C6H13



222, 481, 740,
F
F
n-C6H13
n-C7H15



223, 482, 741,
CF3
H
n-C6H13
CH3



224, 483, 742,
CF3
H
n-C6H13
C2H5



225, 484, 743,
CF3
H
n-C6H13
n-C3H7



226, 485, 744,
CF3
H
n-C6H13
n-C4H9



227, 486, 745,
CF3
H
n-C6H13
n-C5H11



228, 487, 746,
CF3
H
n-C6H13
n-C6H13



229, 488, 747,
CF3
H
n-C6H13
n-C7H15



230, 489, 748,
—OCF3
H
n-C6H13
CH3



231, 490, 749,
—OCF3
H
n-C6H13
C2H5



232, 491, 750,
—OCF3
H
n-C6H13
n-C3H7



233, 492, 751,
—OCF3
H
n-C6H13
n-C4H9



234, 493, 752,
—OCF3
H
n-C6H13
n-C5H11



235, 494, 753,
—OCF3
H
n-C6H13
n-C6H13



236, 495, 754,
—OCF3
H
n-C6H13
n-C7H15



237, 496, 755,
H
H
n-C7H15
n-C7H15



238, 497, 756,
F
H
n-C7H15
CH3



239, 498, 757,
F
H
n-C7H15
C2H5



240, 499, 758,
F
H
n-C7H15
n-C3H7



241, 500, 759,
F
H
n-C7H15
n-C4H9



242, 501, 760,
F
H
n-C7H15
n-C5H11



243, 502, 761,
F
H
n-C7H15
n-C6H13



244, 503, 762,
F
H
n-C7H15
n-C7H15



245, 504, 763,
F
F
n-C7H15
n-C7H15



246, 505, 764,
CF3
H
n-C7H15
CH3



247, 506, 765,
CF3
H
n-C7H15
C2H5



248, 507, 766,
CF3
H
n-C7H15
n-C3H7



249, 508, 767,
CF3
H
n-C7H15
n-C4H9



250, 509, 768,
CF3
H
n-C7H15
n-C5H11



251, 510, 769,
CF3
H
n-C7H15
n-C6H13



252, 511, 770,
CF3
H
n-C7H15
n-C7H15



253, 512, 771,
—OCF3
H
n-C7H15
CH3



254, 513, 772,
—OCF3
H
n-C7H15
C2H5



255, 514, 773,
—OCF3
H
n-C7H15
n-C3H7



256, 515, 774,
—OCF3
H
n-C7H15
n-C4H9



257, 516, 775,
—OCF3
H
n-C7H15
n-C5H11



258, 517, 776,
—OCF3
H
n-C7H15
n-C6H13



259, 518, 777,
—OCF3
H
n-C7H15
n-C7H15










Examples 778-840




Examples 841-903




Examples 904-966




Examples 967-1029
















 











Example No.
R1
R2







778, 841, 904, 967,
H
CH3



779, 842, 905, 968,
H
C2H5



780, 843, 906, 969,
H
n-C3H7



781, 844, 907, 970,
H
n-C4H9



782, 845, 908, 971,
H
n-C5H11



783, 846, 909, 972,
H
n-C6H13



784, 847, 910, 973,
H
n-C7H15



785, 848, 911, 974,
CH3
H



786, 849, 912, 975,
CH3
CH3



787, 850, 913, 976,
CH3
C2H5



788, 851, 914, 977,
CH3
n-C3H7



789, 852, 915, 978,
CH3
n-C4H9



790, 853, 916, 979,
CH3
n-C5H11



791, 854, 917, 980,
CH3
n-C6H13



792, 855, 918, 981,
CH3
n-C7H15



793, 856, 919, 982,
C2H5
H



794, 857, 920, 983,
C2H5
CH3



795, 858, 921, 984,
C2H5
C2H5



796, 859, 922, 985,
C2H5
n-C3H7



797, 860, 923, 986,
C2H5
n-C4H9



798, 861, 924, 987,
C2H5
n-C5H11



799, 862, 925, 988,
C2H5
n-C6H13



800, 863, 926, 989,
C2H5
n-C7H15



801, 864, 927, 990,
n-C3H7
H



802, 865, 928, 991,
n-C3H7
CH3



803, 866, 929, 992,
n-C3H7
C2H5



804, 867, 930, 993,
n-C3H7
n-C3H7



805, 868, 931, 994,
n-C3H7
n-C4H9



806, 869, 932, 995,
n-C3H7
n-C5H11



807, 870, 933, 996,
n-C3H7
n-C6H13



808, 871, 934, 997,
n-C3H7
n-C7H15



809, 872, 935, 998,
n-C4H9
H



810, 873, 936, 999,
n-C4H9
CH3



811, 874, 937, 1000,
n-C4H9
C2H5



812, 875, 938, 1001,
n-C4H9
n-C3H7



813, 876, 939, 1002,
n-C4H9
n-C4H9



814, 877, 940, 1003,
n-C4H9
n-C5H11



815, 878, 941, 1004,
n-C4H9
n-C6H13



816, 879, 942, 1005,
n-C4H9
n-C7H15



817, 880, 943, 1006,
n-C5H11
H



818, 881, 944, 1007,
n-C5H11
CH3



819, 882, 945, 1008,
n-C5H11
C2H5



820, 883, 946, 1009,
n-C5H11
n-C3H7



821, 884, 947, 1010,
n-C5H11
n-C4H9



822, 885, 948, 1011,
n-C5H11
n-C5H11



823, 886, 949, 1012,
n-C5H11
n-C6H13



824, 887, 950, 1013,
n-C5H11
n-C7H15



825, 888, 951, 1014,
n-C6H13
H



826, 889, 952, 1015,
n-C6H13
CH3



827, 890, 953, 1016,
n-C6H13
C2H5



828, 891, 954, 1017,
n-C6H13
n-C3H7



829, 892, 955, 1018,
n-C6H13
n-C4H9



830, 893, 956, 1019,
n-C6H13
n-C5H11



831, 894, 957, 1020,
n-C6H13
n-C6H13



832, 895, 958, 1021,
n-C6H13
n-C7H15



833, 896, 959, 1022,
n-C7H15
H



834, 897, 960, 1023,
n-C7H15
CH3



835, 898, 961, 1024,
n-C7H15
C2H5



836, 899, 962, 1025,
n-C7H15
n-C3H7



837, 900, 963, 1026,
n-C7H15
n-C4H9



838, 901, 964, 1027,
n-C7H15
n-C5H11



839, 902, 965, 1028,
n-C7H15
n-C6H13



840, 903, 966, 1029,
n-C7H15
n-C7H15










Examples 1030-1142




Examples 1143-1255




Examples 1256-1368




Examples 1369-1481
















 












Example No.
R1
R2
Z







1030, 1143, 1256, 1369,
CH3
H
bond



1031, 1144, 1257, 1370,
CH3
CH3
bond



1032, 1145, 1258, 1371,
CH3
C2H5
bond



1033, 1146, 1259, 1372,
CH3
n-C3H7
bond



1034, 1147, 1260, 1373,
CH3
n-C4H9
bond



1035, 1148, 1261, 1374,
CH3
n-C5H11
bond



1036, 1149, 1262, 1375,
CH3
n-C6H13
bond



1037, 1150, 1263, 1376,
CH3
n-C7H15
bond



1038, 1151, 1264, 1377,
CH3
H
CF2CF2



1039, 1152, 1265, 1378,
CH3
CH3
CF2CF2



1040, 1153, 1266, 1379,
CH3
C2H5
CF2CF2



1041, 1154, 1267, 1380,
CH3
n-C3H7
CF2CF2



1042, 1155, 1268, 1381,
CH3
n-C4H9
CF2CF2



1043, 1156, 1269, 1382,
CH3
n-C5H11
CF2CF2



1044, 1157, 1270, 1383,
CH3
n-C6H13
CF2CF2



1045, 1158, 1271, 1384,
CH3
n-C7H15
CF2CF2



1046, 1159, 1272, 1385,
C2H5
H
bond



1047, 1160, 1273, 1386,
C2H5
CH3
bond



1048, 1161, 1274, 1387,
C2H5
C2H5
bond



1049, 1162, 1275, 1388,
C2H5
n-C3H7
bond



1050, 1163, 1276, 1389,
C2H5
n-C4H9
bond



1051, 1164, 1277, 1390,
C2H5
n-C5H11
bond



1052, 1165, 1278, 1391,
C2H5
n-C6H13
bond



1053, 1166, 1279, 1392,
C2H5
n-C7H15
bond



1054, 1167, 1280, 1393,
C2H5
H
CF2CF2



1055, 1168, 1281, 1394,
C2H5
CH3
CF2CF2



1056, 1169, 1282, 1395,
C2H5
C2H5
CF2CF2



1057, 1170, 1283, 1396,
C2H5
n-C3H7
CF2CF2



1058, 1171, 1284, 1397,
C2H5
n-C4H9
CF2CF2



1059, 1172, 1285, 1398,
C2H5
n-C5H11
CF2CF2



1060, 1173, 1286, 1399,
C2H5
n-C6H13
CF2CF2



1061, 1174, 1287, 1400,
C2H5
n-C7H15
CF2CF2



1062, 1175, 1288, 1401,
n-C3H7
H
bond



1063, 1176, 1289, 1402,
n-C3H7
CH3
bond



1064, 1177, 1290, 1403,
n-C3H7
C2H5
bond



1065, 1178, 1291, 1404,
n-C3H7
n-C3H7
bond



1066, 1179, 1292, 1405,
n-C3H7
n-C4H9
bond



1067, 1180, 1293, 1406,
n-C3H7
n-C5H11
bond



1068, 1181, 1294, 1407,
n-C3H7
n-C6H13
bond



1069, 1182, 1295, 1408,
n-C3H7
n-C7H15
bond



1070, 1183, 1296, 1409,
n-C3H7
H
CF2CF2



1071, 1184, 1297, 1410,
n-C3H7
CH3
CF2CF2



1072, 1185, 1298, 1411,
n-C3H7
C2H5
CF2CF2



1073, 1186, 1299, 1412,
n-C3H7
n-C3H7
CF2CF2



1074, 1187, 1300, 1413,
n-C3H7
n-C4H9
CF2CF2



1075, 1188, 1301, 1414,
n-C3H7
n-C5H11
CF2CF2



1076, 1189, 1302, 1415,
n-C3H7
n-C6H13
CF2CF2



1077, 1190, 1303, 1416,
n-C3H7
n-C7H15
CF2CF2



1078, 1191, 1304, 1417,
n-C4H9
H
bond



1079, 1192, 1305, 1418,
n-C4H9
CH3
bond



1080, 1193, 1306, 1419,
n-C4H9
C2H5
bond



1081, 1194, 1307, 1420,
n-C4H9
n-C3H7
bond



1082, 1195, 1308, 1421,
n-C4H9
n-C4H9
bond



1083, 1196, 1309, 1422,
n-C4H9
n-C5H11
bond



1084, 1197, 1310, 1423,
n-C4H9
n-C6H13
bond



1085, 1198, 1311, 1424,
n-C4H9
n-C7H15
bond



1086, 1199, 1312, 1425,
n-C4H9
H
CF2CF2



1087, 1200, 1313, 1426,
n-C4H9
CH3
CF2CF2



1088, 1201, 1314, 1427,
n-C4H9
C2H5
CF2CF2



1089, 1202, 1315, 1428,
n-C4H9
n-C3H7
CF2CF2



1090, 1203, 1316, 1429,
n-C4H9
n-C4H9
CF2CF2



1091, 1204, 1317, 1430,
n-C4H9
n-C5H11
CF2CF2



1092, 1205, 1318, 1431,
n-C4H9
n-C6H13
CF2CF2



1093, 1206, 1319, 1432,
n-C4H9
n-C7H15
CF2CF2



1094, 1207, 1320, 1433,
n-C5H11
n-C7H15
bond



1095, 1208, 1321, 1434,
n-C5H11
H
bond



1096, 1209, 1322, 1435,
n-C5H11
CH3
bond



1097, 1210, 1323, 1436,
n-C5H11
C2H5
bond



1098, 1211, 1324, 1437,
n-C5H11
n-C3H7
bond



1099, 1212, 1325, 1438,
n-C5H11
n-C4H9
bond



1100, 1213, 1326, 1439,
n-C5H11
n-C5H11
bond



1101, 1214, 1327, 1440,
n-C5H11
n-C6H13
bond



1102, 1215, 1328, 1441,
n-C5H11
n-C7H15
bond



1103, 1216, 1329, 1442,
n-C5H11
H
CF2CF2



1104, 1217, 1330, 1443,
n-C5H11
CH3
CF2CF2



1105, 1218, 1331, 1444,
n-C5H11
C2H5
CF2CF2



1106, 1219, 1332, 1445,
n-C5H11
n-C3H7
CF2CF2



1107, 1220, 1333, 1446,
n-C5H11
n-C4H9
CF2CF2



1108, 1221, 1334, 1447,
n-C5H11
n-C5H11
CF2CF2



1109, 1222, 1335, 1448,
n-C5H11
n-C6H13
CF2CF2



1110, 1223, 1336, 1449,
n-C5H11
n-C7H15
CF2CF2



1111, 1224, 1337, 1450,
n-C6H13
H
bond



1112, 1225, 1338, 1451,
n-C6H13
CH3
bond



1113, 1226, 1339, 1452,
n-C6H13
C2H5
bond



1114, 1227, 1340, 1453,
n-C6H13
n-C3H7
bond



1115, 1228, 1341, 1454,
n-C6H13
n-C4H9
bond



1116, 1229, 1342, 1455,
n-C6H13
n-C5H11
bond



1117, 1230, 1343, 1456,
n-C6H13
n-C6H13
bond



1118, 1231, 1344, 1457,
n-C6H13
n-C7H15
bond



1119, 1232, 1345, 1458,
n-C6H13
H
CF2CF2



1120, 1233, 1346, 1459,
n-C6H13
CH3
CF2CF2



1121, 1234, 1347, 1460,
n-C6H13
C2H5
CF2CF2



1122, 1235, 1348, 1461,
n-C6H13
n-C3H7
CF2CF2



1123, 1236, 1349, 1462,
n-C6H13
n-C4H9
CF2CF2



1124, 1237, 1350, 1463,
n-C6H13
n-C5H11
CF2CF2



1125, 1238, 1351, 1464,
n-C6H13
n-C6H13
CF2CF2



1126, 1239, 1352, 1465,
n-C6H13
n-C7H15
CF2CF2



1127, 1240, 1353, 1466,
n-C7H15
H
bond



1128, 1241, 1354, 1467,
n-C7H15
CH3
bond



1129, 1242, 1355, 1468,
n-C7H15
C2H5
bond



1130, 1243, 1356, 1469,
n-C7H15
n-C3H7
bond



1131, 1244, 1357, 1470,
n-C7H15
n-C4H9
bond



1132, 1245, 1358, 1471,
n-C7H15
n-C5H11
bond



1133, 1246, 1359, 1472,
n-C7H15
n-C6H13
bond



1134, 1247, 1360, 1473,
n-C7H15
n-C7H15
bond



1135, 1248, 1361, 1474,
n-C7H15
H
CF2CF2



1136, 1249, 1362, 1475,
n-C7H15
CH3
CF2CF2



1137, 1250, 1363, 1476,
n-C7H15
C2H5
CF2CF2



1138, 1251, 1364, 1477,
n-C7H15
n-C3H7
CF2CF2



1139, 1252, 1365, 1478,
n-C7H15
n-C4H9
CF2CF2



1140, 1253, 1366, 1479,
n-C7H15
n-C5H11
CF2CF2



1141, 1254, 1367, 1480,
n-C7H15
n-C6H13
CF2CF2



1142, 1255, 1368, 1481,
n-C7H15
n-C7H15
CF2CF2










Examples 1482-1594




Examples 1595-1707




Examples 1708-1820




Examples 1821-1933
















 












Example No.
R1
R2
Z







1482, 1595, 1708, 1821,
CH3
H
bond



1483, 1596, 1709, 1822,
CH3
CH3
bond



1484, 1597, 1710, 1823,
CH3
C2H5
bond



1485, 1598, 1711, 1824,
CH3
n-C3H7
bond



1486, 1599, 1712, 1825,
CH3
n-C4H9
bond



1487, 1600, 1713, 1826,
CH3
n-C5H11
bond



1488, 1601, 1714, 1827,
CH3
n-C6H13
bond



1489, 1602, 1715, 1828,
CH3
n-C7H15
bond



1490, 1603, 1716, 1829,
CH3
H
CF2CF2



1491, 1604, 1717, 1830,
CH3
CH3
CF2CF2



1492, 1605, 1718, 1831,
CH3
C2H5
CF2CF2



1493, 1606, 1719, 1832,
CH3
n-C3H7
CF2CF2



1494, 1607, 1720, 1833,
CH3
n-C4H9
CF2CF2



1495, 1608, 1721, 1834,
CH3
n-C5H11
CF2CF2



1496, 1609, 1722, 1835,
CH3
n-C6H13
CF2CF2



1497, 1610, 1723, 1836,
CH3
n-C7H15
CF2CF2



1498, 1611, 1724, 1837,
C2H5
H
bond



1499, 1612, 1725, 1838,
C2H5
CH3
bond



1500, 1613, 1726, 1839,
C2H5
C2H5
bond



1501, 1614, 1727, 1840,
C2H5
n-C3H7
bond



1502, 1615, 1728, 1841,
C2H5
n-C4H9
bond



1503, 1616, 1729, 1842,
C2H5
n-C5H11
bond



1504, 1617, 1730, 1843,
C2H5
n-C6H13
bond



1505, 1618, 1731, 1844,
C2H5
n-C7H15
bond



1506, 1619, 1732, 1845,
C2H5
H
CF2CF2



1507, 1620, 1733, 1846,
C2H5
CH3
CF2CF2



1508, 1621, 1734, 1847,
C2H5
C2H5
CF2CF2



1509, 1622, 1735, 1848,
C2H5
n-C3H7
CF2CF2



1510, 1623, 1736, 1849,
C2H5
n-C4H9
CF2CF2



1511, 1624, 1737, 1850,
C2H5
n-C5H11
CF2CF2



1512, 1625, 1738, 1851,
C2H5
n-C6H13
CF2CF2



1513, 1626, 1739, 1852,
C2H5
n-C7H15
CF2CF2



1514, 1627, 1740, 1853,
n-C3H7
H
bond



1515, 1628, 1741, 1854,
n-C3H7
CH3
bond



1516, 1629, 1742, 1855,
n-C3H7
C2H5
bond



1517, 1630, 1743, 1856,
n-C3H7
n-C3H7
bond



1518, 1631, 1744, 1857,
n-C3H7
n-C4H9
bond



1519, 1632, 1745, 1858,
n-C3H7
n-C5H11
bond



1520, 1633, 1746, 1859,
n-C3H7
n-C6H13
bond



1521, 1634, 1747, 1860,
n-C3H7
n-C7H15
bond



1522, 1635, 1748, 1861,
n-C3H7
H
CF2CF2



1523, 1636, 1749, 1862,
n-C3H7
CH3
CF2CF2



1524, 1637, 1750, 1863,
n-C3H7
C2H5
CF2CF2



1525, 1638, 1751, 1864,
n-C3H7
n-C3H7
CF2CF2



1526, 1639, 1752, 1865,
n-C3H7
n-C4H9
CF2CF2



1527, 1640, 1753, 1866,
n-C3H7
n-C5H11
CF2CF2



1528, 1641, 1754, 1867,
n-C3H7
n-C6H13
CF2CF2



1529, 1642, 1755, 1868,
n-C3H7
n-C7H15
CF2CF2



1530, 1643, 1756, 1869,
n-C4H9
H
bond



1531, 1644, 1757, 1870,
n-C4H9
CH3
bond



1532, 1645, 1758, 1871,
n-C4H9
C2H5
bond



1533, 1646, 1759, 1872,
n-C4H9
n-C3H7
bond



1534, 1647, 1760, 1873,
n-C4H9
n-C4H9
bond



1535, 1648, 1761, 1874,
n-C4H9
n-C5H11
bond



1536, 1649, 1762, 1875,
n-C4H9
n-C6H13
bond



1537, 1650, 1763, 1876,
n-C4H9
n-C7H15
bond



1538, 1651, 1764, 1877,
n-C4H9
H
CF2CF2



1539, 1652, 1765, 1878,
n-C4H9
CH3
CF2CF2



1540, 1653, 1766, 1879,
n-C4H9
C2H5
CF2CF2



1541, 1654, 1767, 1880,
n-C4H9
n-C3H7
CF2CF2



1542, 1655, 1768, 1881,
n-C4H9
n-C4H9
CF2CF2



1543, 1656, 1769, 1882,
n-C4H9
n-C5H11
CF2CF2



1544, 1657, 1770, 1883,
n-C4H9
n-C6H13
CF2CF2



1545, 1658, 1771, 1884,
n-C4H9
n-C7H15
CF2CF2



1546, 1659, 1772, 1885,
n-C5H11
n-C7H15
bond



1547, 1660, 1773, 1886,
n-C5H11
H
bond



1548, 1661, 1774, 1887,
n-C5H11
CH3
bond



1549, 1662, 1775, 1888,
n-C5H11
C2H5
bond



1550, 1663, 1776, 1889,
n-C5H11
n-C3H7
bond



1551, 1664, 1777, 1890,
n-C5H11
n-C4H9
bond



1552, 1665, 1778, 1891,
n-C5H11
n-C5H11
bond



1553, 1666, 1779, 1892,
n-C5H11
n-C6H13
bond



1554, 1667, 1780, 1893,
n-C5H11
n-C7H15
bond



1555, 1668, 1781, 1894,
n-C5H11
H
CF2CF2



1556, 1669, 1782, 1895,
n-C5H11
CH3
CF2CF2



1557, 1670, 1783, 1896,
n-C5H11
C2H5
CF2CF2



1558, 1671, 1784, 1897,
n-C5H11
n-C3H7
CF2CF2



1559, 1672, 1785, 1898,
n-C5H11
n-C4H9
CF2CF2



1560, 1673, 1786, 1899,
n-C5H11
n-C5H11
CF2CF2



1561, 1674, 1787, 1900,
n-C5H11
n-C6H13
CF2CF2



1562, 1675, 1788, 1901,
n-C5H11
n-C7H15
CF2CF2



1563, 1676, 1789, 1902,
n-C6H13
H
bond



1564, 1677, 1790, 1903,
n-C6H13
CH3
bond



1565, 1678, 1791, 1904,
n-C6H13
C2H5
bond



1566, 1679, 1792, 1905,
n-C6H13
n-C3H7
bond



1567, 1680, 1793, 1906,
n-C6H13
n-C4H9
bond



1568, 1681, 1794, 1907,
n-C6H13
n-C5H11
bond



1569, 1682, 1795, 1908,
n-C6H13
n-C6H13
bond



1570, 1683, 1796, 1909,
n-C6H13
n-C7H15
bond



1571, 1684, 1797, 1910,
n-C6H13
H
CF2CF2



1572, 1685, 1798, 1911,
n-C6H13
CH3
CF2CF2



1573, 1686, 1799, 1912,
n-C6H13
C2H5
CF2CF2



1574, 1687, 1800, 1913,
n-C6H13
n-C3H7
CF2CF2



1575, 1688, 1801, 1914,
n-C6H13
n-C4H9
CF2CF2



1576, 1689, 1802, 1915,
n-C6H13
n-C5H11
CF2CF2



1577, 1690, 1803, 1916,
n-C6H13
n-C6H13
CF2CF2



1578, 1691, 1804, 1917,
n-C6H13
n-C7H15
CF2CF2



1579, 1692, 1805, 1918,
n-C7H15
H
bond



1580, 1693, 1806, 1919,
n-C7H15
CH3
bond



1581, 1694, 1807, 1920,
n-C7H15
C2H5
bond



1582, 1695, 1808, 1921,
n-C7H15
n-C3H7
bond



1583, 1696, 1809, 1922,
n-C7H15
n-C4H9
bond



1584, 1697, 1810, 1923,
n-C7H15
n-C5H11
bond



1585, 1698, 1811, 1924,
n-C7H15
n-C6H13
bond



1586, 1699, 1812, 1925,
n-C7H15
n-C7H15
bond



1587, 1700, 1813, 1926,
n-C7H15
H
CF2CF2



1588, 1701, 1814, 1927,
n-C7H15
CH3
CF2CF2



1589, 1702, 1815, 1928,
n-C7H15
C2H5
CF2CF2



1590, 1703, 1816, 1929,
n-C7H15
n-C3H7
CF2CF2



1591, 1704, 1817, 1930,
n-C7H15
n-C4H9
CF2CF2



1592, 1705, 1818, 1931,
n-C7H15
n-C5H11
CF2CF2



1593, 1706, 1819, 1932,
n-C7H15
n-C6H13
CF2CF2



1594, 1707, 1820, 1933,
n-C7H15
n-C7H15
CF2CF2










Examples 1934-1958




Examples 1959-1983




Examples 1984-2008




Examples 2009-2033
















 












Example No.
L1
L2
R2







1934, 1959, 1984, 2009,
H
H
H



1935, 1960, 1985, 2010,
F
H
H



1936, 1961, 1986, 2011,
F
F
H



1937, 1962, 1987, 2012,
F
F
H



1938, 1963, 1988, 2013,
H
H
CH3



1939, 1964, 1989, 2014,
F
H
CH3



1940, 1965, 1990, 2015,
F
F
CH3



1941, 1966, 1991, 2016,
H
H
C2H5



1942, 1967, 1992, 2017,
F
H
C2H5



1943, 1968, 1993, 2018,
F
F
C2H5



1944, 1969, 1994, 2019,
H
H
n-C3H7



1945, 1970, 1995, 2020,
F
H
n-C3H7



1946, 1971, 1996, 2021,
F
F
n-C3H7



1947, 1972, 1997, 2022,
H
H
n-C4H9



1948, 1973, 1998, 2023,
F
H
n-C4H9



1949, 1974, 1999, 2024,
F
F
n-C4H9



1950, 1975, 2000, 2025,
H
H
n-C5H11



1951, 1976, 2001, 2026,
F
H
n-C5H11



1952, 1977, 2002, 2027,
F
F
n-C5H11



1953, 1978, 2003, 2028,
H
H
n-C6H13



1954, 1979, 2004, 2029,
F
H
n-C6H13



1955, 1980, 2005, 2030,
F
F
n-C6H13



1956, 1981, 2006, 2031,
H
H
n-C7H15



1957, 1982, 2007, 2032,
F
H
n-C7H15



1958, 1983, 2008, 2033,
F
F
n-C7H15










Examples 2034-2058




Examples 2059-2083




Examples 2084-2108




Examples 2109-2133
















 












Example No.
L1
L2
R2







2034, 2059, 2084, 2109,
H
H
H



2035, 2060, 2085, 2110,
F
H
H



2036, 2061, 2086, 2111,
F
F
H



2037, 2062, 2087, 2112,
F
F
H



2038, 2063, 2088, 2113,
H
H
CH3



2039, 2064, 2089, 2114,
F
H
CH3



2040, 2065, 2090, 2115,
F
F
CH3



2041, 2066, 2091, 2116,
H
H
C2H5



2042, 2067, 2092, 2117,
F
H
C2H5



2043, 2068, 2093, 2118,
F
F
C2H5



2044, 2069, 2094, 2119,
H
H
n-C3H7



2045, 2070, 2095, 2120,
F
H
n-C3H7



2046, 2071, 2096, 2121,
F
F
n-C3H7



2047, 2072, 2097, 2122,
H
H
n-C4H9



2048, 2073, 2098, 2123,
F
H
n-C4H9



2049, 2074, 2099, 2124,
F
F
n-C4H9



2050, 2075, 2100, 2125,
H
H
n-C5H11



2051, 2076, 2101, 2126,
F
H
n-C5H11



2052, 2077, 2102, 2127,
F
F
n-C5H11



2053, 2078, 2103, 2128,
H
H
n-C6H13



2054, 2079, 2104, 2129,
F
H
n-C6H13



2055, 2080, 2105, 2130,
F
F
n-C6H13



2056, 2081, 2106, 2131,
H
H
n-C7H15



2057, 2082, 2107, 2132,
F
H
n-C7H15



2058, 2083, 2108, 2133,
F
F
n-C7H15










Examples 2134-2189




Examples 2190-2245




Examples 2246-2301




Examples 2302-2357
















 











Example No.
R2
R3







2134, 2190, 2246, 2302,
H
CH3



2135, 2191, 2247, 2303,
H
C2H5



2136, 2192, 2248, 2304,
H
n-C3H7



2137, 2193, 2249, 2305,
H
n-C4H9



2138, 2194, 2250, 2306,
H
n-C5H11



2139, 2195, 2251, 2307,
H
n-C6H13



2140, 2196, 2252, 2308,
H
n-C7H15



2141, 2197, 2253, 2309,
CH3
CH3



2142, 2198, 2254, 2310,
CH3
C2H5



2143, 2199, 2255, 2311,
CH3
n-C3H7



2144, 2200, 2256, 2312,
CH3
n-C4H9



2145, 2201, 2257, 2313,
CH3
n-C5H11



2146, 2202, 2258, 2314,
CH3
n-C6H13



2147, 2203, 2259, 2315,
CH3
n-C7H15



2148, 2204, 2260, 2316,
C2H5
CH3



2149, 2205, 2261, 2317,
C2H5
C2H5



2150, 2206, 2262, 2318,
C2H5
n-C3H7



2151, 2207, 2263, 2319,
C2H5
n-C4H9



2152, 2208, 2264, 2320,
C2H5
n-C5H11



2153, 2209, 2265, 2321,
C2H5
n-C6H13



2154, 2210, 2266, 2322,
C2H5
n-C7H15



2155, 2211, 2267, 2323,
n-C3H7
CH3



2156, 2212, 2268, 2324,
n-C3H7
C2H5



2157, 2213, 2269, 2325,
n-C3H7
n-C3H7



2158, 2214, 2270, 2326,
n-C3H7
n-C4H9



2159, 2215, 2271, 2327,
n-C3H7
n-C5H11



2160, 2216, 2272, 2328,
n-C3H7
n-C6H13



2161, 2217, 2273, 2329,
n-C3H7
n-C7H15



2162, 2218, 2274, 2330,
n-C4H9
CH3



2163, 2219, 2275, 2331,
n-C4H9
C2H5



2164, 2220, 2276, 2332,
n-C4H9
n-C3H7



2165, 2221, 2277, 2333,
n-C4H9
n-C4H9



2166, 2222, 2278, 2334,
n-C4H9
n-C5H11



2167, 2223, 2279, 2335,
n-C4H9
n-C6H13



2168, 2224, 2280, 2336,
n-C4H9
n-C7H15



2169, 2225, 2281, 2337,
n-C5H11
CH3



2170, 2226, 2282, 2338,
n-C5H11
C2H5



2171, 2227, 2283, 2339,
n-C5H11
n-C3H7



2172, 2228, 2284, 2340,
n-C5H11
n-C4H9



2173, 2229, 2285, 2341,
n-C5H11
n-C5H11



2174, 2230, 2286, 2342,
n-C5H11
n-C6H13



2175, 2231, 2287, 2343,
n-C5H11
n-C7H15



2176, 2232, 2288, 2344,
n-C6H13
CH3



2177, 2233, 2289, 2345,
n-C6H13
C2H5



2178, 2234, 2290, 2346,
n-C6H13
n-C3H7



2179, 2235, 2291, 2347,
n-C6H13
n-C4H9



2180, 2236, 2292, 2348,
n-C6H13
n-C5H11



2181, 2237, 2293, 2349,
n-C6H13
n-C6H13



2182, 2238, 2294, 2350,
n-C6H13
n-C7H15



2183, 2239, 2295, 2351,
n-C7H15
CH3



2184, 2240, 2296, 2352,
n-C7H15
C2H5



2185, 2241, 2297, 2353,
n-C7H15
n-C3H7



2186, 2242, 2298, 2354,
n-C7H15
n-C4H9



2187, 2243, 2299, 2355,
n-C7H15
n-C5H11



2188, 2244, 2300, 2356,
n-C7H15
n-C6H13



2189, 2245, 2301, 2357,
n-C7H15
n-C7H15










Examples 2358-2621




Examples 2622-2885
















 













Example No.
X1
X2
R1
R2







2358, 2622,
H
H
H
H



2359, 2623,
H
H
H
CH3



2360, 2624,
H
H
H
C2H5



2361, 2625,
H
H
H
n-C3H7



2362, 2626,
H
H
H
n-C4H9



2363, 2627,
H
H
H
n-C5H11



2364, 2628,
H
H
H
n-C6H13



2365, 2629,
H
H
H
n-C7H15



2366, 2630,
F
H
H
H



2367, 2631,
F
H
H
CH3



2368, 2632,
F
H
H
C2H5



2369, 2633,
F
H
H
n-C3H7



2370, 2634,
F
H
H
n-C4H9



2371, 2635,
F
H
H
n-C5H11



2372, 2636,
F
H
H
n-C6H13



2373, 2637,
F
H
H
n-C7H15



2374, 2638,
F
F
H
H



2375, 2639,
F
F
H
CH3



2376, 2640,
F
F
H
C2H5



2377, 2641,
F
F
H
n-C3H7



2378, 2642,
F
F
H
n-C4H9



2379, 2643,
F
F
H
n-C5H11



2380, 2644,
F
F
H
n-C6H13



2381, 2645,
F
F
H
n-C7H15



2382, 2646,
CF3
H
H
H



2383, 2647,
CF3
H
H
CH3



2384, 2648,
CF3
H
H
C2H5



2385, 2649,
CF3
H
H
n-C3H7



2386, 2650,
CF3
H
H
n-C4H9



2387, 2651,
CF3
H
H
n-C5H11



2388, 2652,
CF3
H
H
n-C6H13



2389, 2653,
CF3
H
H
n-C7H15



2390, 2654,
—OCF3
H
H
H



2391, 2655,
—OCF3
H
H
CH3



2392, 2656,
—OCF3
H
H
C2H5



2393, 2657,
—OCF3
H
H
n-C3H7



2394, 2658,
—OCF3
H
H
n-C4H9



2395, 2659,
—OCF3
H
H
n-C5H11



2396, 2660,
—OCF3
H
H
n-C6H13



2397, 2661,
—OCF3
H
H
n-C7H15



2398, 2662,
H
H
CH3
CH3



2399, 2663,
H
H
CH3
C2H5



2400, 2664,
H
H
CH3
n-C3H7



2401, 2665,
H
H
CH3
n-C4H9



2402, 2666,
H
H
CH3
n-C5H11



2403, 2667,
H
H
CH3
n-C6H13



2404, 2668,
H
H
CH3
n-C7H15



2405, 2669,
F
H
CH3
H



2406, 2670,
F
H
CH3
CH3



2407, 2671,
F
H
CH3
C2H5



2408, 2672,
F
H
CH3
n-C3H7



2409, 2673,
F
H
CH3
n-C4H9



2410, 2674,
F
H
CH3
n-C5H11



2411, 2675,
F
H
CH3
n-C6H13



2412, 2676,
F
H
CH3
n-C7H15



2413, 2677,
F
F
CH3
CH3



2414, 2678,
F
F
CH3
C2H5



2415, 2679,
F
F
CH3
n-C3H7



2416, 2680,
F
F
CH3
n-C4H9



2417, 2681,
F
F
CH3
n-C5H11



2418, 2682,
F
F
CH3
n-C6H13



2419, 2683,
F
F
CH3
n-C7H15



2420, 2684,
CF3
H
CH3
H



2421, 2685,
CF3
H
CH3
CH3



2422, 2686,
CF3
H
CH3
C2H5



2423, 2687,
CF3
H
CH3
n-C3H7



2424, 2688,
CF3
H
CH3
n-C4H9



2425, 2689,
CF3
H
CH3
n-C5H11



2426, 2690,
CF3
H
CH3
n-C6H13



2427, 2691,
CF3
H
CH3
n-C7H15



2428, 2692,
—OCF3
H
CH3
H



2429, 2693,
—OCF3
H
CH3
CH3



2430, 2694,
—OCF3
H
CH3
C2H5



2431, 2695,
—OCF3
H
CH3
n-C3H7



2432, 2696,
—OCF3
H
CH3
n-C4H9



2433, 2697,
—OCF3
H
CH3
n-C5H11



2434, 2698,
—OCF3
H
CH3
n-C6H13



2435, 2699,
—OCF3
H
CH3
n-C7H15



2436, 2700,
H
H
C2H5
C2H5



2437, 2701,
H
H
C2H5
n-C3H7



2438, 2702,
H
H
C2H5
n-C4H9



2439, 2703,
H
H
C2H5
n-C5H11



2440, 2704,
H
H
C2H5
n-C6H13



2441, 2705,
H
H
C2H5
n-C7H15



2442, 2706,
F
H
C2H5
H



2443, 2707,
F
H
C2H5
CH3



2444, 2708,
F
H
C2H5
C2H5



2445, 2709,
F
H
C2H5
n-C3H7



2446, 2710,
F
H
C2H5
n-C4H9



2447, 2711,
F
H
C2H5
n-C5H11



2448, 2712,
F
H
C2H5
n-C6H13



2449, 2713,
F
H
C2H5
n-C7H15



2450, 2714,
F
F
C2H5
C2H5



2451, 2715,
F
F
C2H5
n-C3H7



2452, 2716,
F
F
C2H5
n-C4H9



2453, 2717,
F
F
C2H5
n-C5H11



2454, 2718,
F
F
C2H5
n-C6H13



2455, 2719,
F
F
C2H5
n-C7H15



2456, 2720,
CF3
H
C2H5
H



2457, 2721,
CF3
H
C2H5
CH3



2458, 2722,
CF3
H
C2H5
C2H5



2459, 2723,
CF3
H
C2H5
n-C3H7



2460, 2724,
CF3
H
C2H5
n-C4H9



2461, 2725,
CF3
H
C2H5
n-C5H11



2462, 2726,
CF3
H
C2H5
n-C6H13



2463, 2727,
CF3
H
C2H5
n-C7H15



2464, 2728,
—OCF3
H
C2H5
H



2465, 2729,
—OCF3
H
C2H5
CH3



2466, 2730,
—OCF3
H
C2H5
C2H5



2467, 2731,
—OCF3
H
C2H5
n-C3H7



2468, 2732,
—OCF3
H
C2H5
n-C4H9



2469, 2733,
—OCF3
H
C2H5
n-C5H11



2470, 2734,
—OCF3
H
C2H5
n-C6H13



2471, 2735,
—OCF3
H
C2H5
n-C7H15



2472, 2736,
H
H
n-C3H7
n-C3H7



2473, 2737,
H
H
n-C3H7
n-C4H9



2474, 2738,
H
H
n-C3H7
n-C5H11



2475, 2739,
H
H
n-C3H7
n-C6H13



2476, 2740,
H
H
n-C3H7
n-C7H15



2477, 2741,
F
H
n-C3H7
H



2478, 2742,
F
H
n-C3H7
CH3



2479, 2743,
F
H
n-C3H7
C2H5



2480, 2744,
F
H
n-C3H7
n-C3H7



2481, 2745,
F
H
n-C3H7
n-C4H9



2482, 2746,
F
H
n-C3H7
n-C5H11



2483, 2747,
F
H
n-C3H7
n-C6H13



2484, 2748,
F
H
n-C3H7
n-C7H15



2485, 2749,
F
F
n-C3H7
n-C3H7



2486, 2750,
F
F
n-C3H7
n-C4H9



2487, 2751,
F
F
n-C3H7
n-C5H11



2488, 2752,
F
F
n-C3H7
n-C6H13



2489, 2753,
F
F
n-C3H7
n-C7H15



2490, 2754,
CF3
H
n-C3H7
H



2491, 2755,
CF3
H
n-C3H7
CH3



2492, 2756,
CF3
H
n-C3H7
C2H5



2493, 2757,
CF3
H
n-C3H7
n-C3H7



2494, 2758,
CF3
H
n-C3H7
n-C4H9



2495, 2759,
CF3
H
n-C3H7
n-C5H11



2496, 2760,
CF3
H
n-C3H7
n-C6H13



2497, 2761,
CF3
H
n-C3H7
n-C7H15



2498, 2762,
—OCF3
H
n-C3H7
H



2499, 2763,
—OCF3
H
n-C3H7
CH3



2500, 2764,
—OCF3
H
n-C3H7
C2H5



2501, 2765,
—OCF3
H
n-C3H7
n-C3H7



2502, 2766,
—OCF3
H
n-C3H7
n-C4H9



2503, 2767,
—OCF3
H
n-C3H7
n-C5H11



2504, 2768,
—OCF3
H
n-C3H7
n-C6H13



2505, 2769,
—OCF3
H
n-C3H7
n-C7H15



2506, 2770,
H
H
n-C4H9
n-C4H9



2507, 2771,
H
H
n-C4H9
n-C5H11



2508, 2772,
H
H
n-C4H9
n-C6H13



2509, 2773,
H
H
n-C4H9
n-C7H15



2510, 2774,
F
H
n-C4H9
H



2511, 2775,
F
H
n-C4H9
CH3



2512, 2776,
F
H
n-C4H9
C2H5



2513, 2777,
F
H
n-C4H9
n-C3H7



2514, 2778,
F
H
n-C4H9
n-C4H9



2515, 2779,
F
H
n-C4H9
n-C5H11



2516, 2780,
F
H
n-C4H9
n-C6H13



2517, 2781,
F
H
n-C4H9
n-C7H15



2518, 2782,
F
F
n-C4H9
n-C4H9



2519, 2783,
F
F
n-C4H9
n-C5H11



2520, 2784,
F
F
n-C4H9
n-C6H13



2521, 2785,
F
F
n-C4H9
n-C7H15



2522, 2786,
CF3
H
n-C4H9
H



2523, 2787,
CF3
H
n-C4H9
CH3



2524, 2788,
CF3
H
n-C4H9
C2H5



2525, 2789,
CF3
H
n-C4H9
n-C3H7



2526, 2790,
CF3
H
n-C4H9
n-C4H9



2527, 2791,
CF3
H
n-C4H9
n-C5H11



2528, 2792,
CF3
H
n-C4H9
n-C6H13



2529, 2793,
CF3
H
n-C4H9
n-C7H15



2530, 2794,
—OCF3
H
n-C4H9
H



2531, 2795,
—OCF3
H
n-C4H9
CH3



2532, 2796,
—OCF3
H
n-C4H9
C2H5



2533, 2797,
—OCF3
H
n-C4H9
n-C3H7



2534, 2798,
—OCF3
H
n-C4H9
n-C4H9



2535, 2799,
—OCF3
H
n-C4H9
n-C5H11



2536, 2800,
—OCF3
H
n-C4H9
n-C6H13



2537, 2801,
—OCF3
H
n-C4H9
n-C7H15



2538, 2802,
H
H
n-C5H11
n-C5H11



2539, 2803,
H
H
n-C5H11
n-C6H13



2540, 2804,
H
H
n-C5H11
n-C7H15



2541, 2805,
F
H
n-C5H11
H



2542, 2806,
F
H
n-C5H11
CH3



2543, 2807,
F
H
n-C5H11
C2H5



2544, 2808,
F
H
n-C5H11
n-C3H7



2545, 2809,
F
H
n-C5H11
n-C4H9



2546, 2810,
F
H
n-C5H11
n-C5H11



2547, 2811,
F
H
n-C5H11
n-C6H13



2548, 2812,
F
H
n-C5H11
n-C7H15



2549, 2813,
F
F
n-C5H11
n-C5H11



2550, 2814,
F
F
n-C5H11
n-C6H13



2551, 2815,
F
F
n-C5H11
n-C7H15



2552, 2816,
CF3
H
n-C5H11
H



2553, 2817,
CF3
H
n-C5H11
CH3



2554, 2818,
CF3
H
n-C5H11
C2H5



2555, 2819,
CF3
H
n-C5H11
n-C3H7



2556, 2820,
CF3
H
n-C5H11
n-C4H9



2557, 2821,
CF3
H
n-C5H11
n-C5H11



2558, 2822,
CF3
H
n-C5H11
n-C6H13



2559, 2823,
CF3
H
n-C5H11
n-C7H15



2560, 2824,
—OCF3
H
n-C5H11
H



2561, 2825,
—OCF3
H
n-C5H11
CH3



2562, 2826,
—OCF3
H
n-C5H11
C2H5



2563, 2827,
—OCF3
H
n-C5H11
n-C3H7



2564, 2828,
—OCF3
H
n-C5H11
n-C4H9



2565, 2829,
—OCF3
H
n-C5H11
n-C5H11



2566, 2830,
—OCF3
H
n-C5H11
n-C6H13



2567, 2831,
—OCF3
H
n-C5H11
n-C7H15



2568, 2832,
H
H
n-C6H13
n-C6H13



2569, 2833,
H
H
n-C6H13
n-C7H15



2570, 2834,
F
H
n-C6H13
H



2571, 2835,
F
H
n-C6H13
CH3



2572, 2836,
F
H
n-C6H13
C2H5



2573, 2837,
F
H
n-C6H13
n-C3H7



2574, 2838,
F
H
n-C6H13
n-C4H9



2575, 2839,
F
H
n-C6H13
n-C5H11



2576, 2840,
F
H
n-C6H13
n-C6H13



2577, 2841,
F
H
n-C6H13
n-C7H15



2578, 2842,
F
F
n-C6H13
n-C6H13



2579, 2843,
F
F
n-C6H13
n-C7H15



2580, 2844,
CF3
H
n-C6H13
H



2581, 2845,
CF3
H
n-C6H13
CH3



2582, 2846,
CF3
H
n-C6H13
C2H5



2583, 2847,
CF3
H
n-C6H13
n-C3H7



2584, 2848,
CF3
H
n-C6H13
n-C4H9



2585, 2849,
CF3
H
n-C6H13
n-C5H11



2586, 2850,
CF3
H
n-C6H13
n-C6H13



2587, 2851,
CF3
H
n-C6H13
n-C7H15



2588, 2852,
—OCF3
H
n-C6H13
H



2589, 2853,
—OCF3
H
n-C6H13
CH3



2590, 2854,
—OCF3
H
n-C6H13
C2H5



2591, 2855,
—OCF3
H
n-C6H13
n-C3H7



2592, 2856,
—OCF3
H
n-C6H13
n-C4H9



2593, 2857,
—OCF3
H
n-C6H13
n-C5H11



2594, 2858,
—OCF3
H
n-C6H13
n-C6H13



2595, 2859,
—OCF3
H
n-C6H13
n-C7H15



2596, 2860,
H
H
n-C7H15
n-C7H15



2597, 2861,
F
H
n-C7H15
H



2598, 2862,
F
H
n-C7H15
CH3



2599, 2863,
F
H
n-C7H15
C2H5



2600, 2864,
F
H
n-C7H15
n-C3H7



2601, 2865,
F
H
n-C7H15
n-C4H9



2602, 2866,
F
H
n-C7H15
n-C5H11



2603, 2867,
F
H
n-C7H15
n-C6H13



2604, 2868,
F
H
n-C7H15
n-C7H15



2605, 2869,
F
F
n-C7H15
n-C7H15



2606, 2870,
CF3
H
n-C7H15
H



2607, 2871,
CF3
H
n-C7H15
CH3



2608, 2872,
CF3
H
n-C7H15
C2H5



2609, 2873,
CF3
H
n-C7H15
n-C3H7



2610, 2874,
CF3
H
n-C7H15
n-C4H9



2611, 2875,
CF3
H
n-C7H15
n-C5H11



2612, 2876,
CF3
H
n-C7H15
n-C6H13



2613, 2877,
CF3
H
n-C7H15
n-C7H15



2614, 2878,
—OCF3
H
n-C7H15
H



2615, 2879,
—OCF3
H
n-C7H15
CH3



2616, 2880,
—OCF3
H
n-C7H15
C2H5



2617, 2881,
—OCF3
H
n-C7H15
n-C3H7



2618, 2882,
—OCF3
H
n-C7H15
n-C4H9



2619, 2883,
—OCF3
H
n-C7H15
n-C5H11



2620, 2884,
—OCF3
H
n-C7H15
n-C6H13



2621, 2885,
—OCF3
H
n-C7H15
n-C7H15










Examples 2886-2949




Examples 2950-3013




Examples 3014-3077




Examples 3078-3141
















 











Example No.
R1
R2







2886, 2950, 3014, 3078,
H
H



2887, 2951, 3015, 3079,
H
CH3



2888, 2952, 3016, 3080,
H
C2H5



2889, 2953, 3017, 3081,
H
n-C3H7



2890, 2954, 3018, 3082,
H
n-C4H9



2891, 2955, 3019, 3083,
H
n-C5H11



2892, 2956, 3020, 3084,
H
n-C6H13



2893, 2957, 3021, 3085,
H
n-C7H15



2894, 2958, 3022, 3086,
CH3
H



2895, 2959, 3023, 3087,
CH3
CH3



2896, 2960, 3024, 3088,
CH3
C2H5



2897, 2961, 3025, 3089,
CH3
n-C3H7



2898, 2962, 3026, 3090,
CH3
n-C4H9



2899, 2963, 3027, 3091,
CH3
n-C5H11



2900, 2964, 3028, 3092,
CH3
n-C6H13



2901, 2965, 3029, 3093,
CH3
n-C7H15



2902, 2966, 3030, 3094,
C2H5
H



2903, 2967, 3031, 3095,
C2H5
CH3



2904, 2968, 3032, 3096,
C2H5
C2H5



2905, 2969, 3033, 3097,
C2H5
n-C3H7



2906, 2970, 3034, 3098,
C2H5
n-C4H9



2907, 2971, 3035, 3099,
C2H5
n-C5H11



2908, 2972, 3036, 3100,
C2H5
n-C6H13



2909, 2973, 3037, 3101,
C2H5
n-C7H15



2910, 2974, 3038, 3102,
n-C3H7
H



2911, 2975, 3039, 3103,
n-C3H7
CH3



2912, 2976, 3040, 3104,
n-C3H7
C2H5



2913, 2977, 3041, 3105,
n-C3H7
n-C3H7



2914, 2978, 3042, 3106,
n-C3H7
n-C4H9



2915, 2979, 3043, 3107,
n-C3H7
n-C5H11



2916, 2980, 3044, 3108,
n-C3H7
n-C6H13



2917, 2981, 3045, 3109,
n-C3H7
n-C7H15



2918, 2982, 3046, 3110,
n-C4H9
H



2919, 2983, 3047, 3111,
n-C4H9
CH3



2920, 2984, 3048, 3112,
n-C4H9
C2H5



2921, 2985, 3049, 3113,
n-C4H9
n-C3H7



2922, 2986, 3050, 3114,
n-C4H9
n-C4H9



2923, 2987, 3051, 3115,
n-C4H9
n-C5H11



2924, 2988, 3052, 3116,
n-C4H9
n-C6H13



2925, 2989, 3053, 3117,
n-C4H9
n-C7H15



2926, 2990, 3054, 3118,
n-C5H11
H



2927, 2991, 3055, 3119,
n-C5H11
CH3



2928, 2992, 3056, 3120,
n-C5H11
C2H5



2929, 2993, 3057, 3121,
n-C5H11
n-C3H7



2930, 2994, 3058, 3122,
n-C5H11
n-C4H9



2931, 2995, 3059, 3123,
n-C5H11
n-C5H11



2932, 2996, 3060, 3124,
n-C5H11
n-C6H13



2933, 2997, 3061, 3125,
n-C5H11
n-C7H15



2934, 2998, 3062, 3126,
n-C6H13
H



2935, 2999, 3063, 3127,
n-C6H13
CH3



2936, 3000, 3064, 3128,
n-C6H13
C2H5



2937, 3001, 3065, 3129,
n-C6H13
n-C3H7



2938, 3002, 3066, 3130,
n-C6H13
n-C4H9



2939, 3003, 3067, 3131,
n-C6H13
n-C5H11



2940, 3004, 3068, 3132,
n-C6H13
n-C6H13



2941, 3005, 3069, 3133,
n-C6H13
n-C7H15



2942, 3006, 3070, 3134,
n-C7H15
H



2943, 3007, 3071, 3135,
n-C7H15
CH3



2944, 3008, 3072, 3136,
n-C7H15
C2H5



2945, 3009, 3073, 3137,
n-C7H15
n-C3H7



2946, 3010, 3074, 3138,
n-C7H15
n-C4H9



2947, 3011, 3075, 3139,
n-C7H15
n-C5H11



2948, 3012, 3076, 3140,
n-C7H15
n-C6H13



2949, 3013, 3077, 3141,
n-C7H15
n-C7H15










Examples 3142-3205




Examples 3206-3269




Examples 3270-3333




Examples 3334-3397
















 











Example No.
R1
R2







3142, 3206, 3270, 3334,
H
H



3143, 3207, 3271, 3335,
H
CH3



3144, 3208, 3272, 3336,
H
C2H5



3145, 3209, 3273, 3337,
H
n-C3H7



3146, 3210, 3274, 3338,
H
n-C4H9



3147, 3211, 3275, 3339,
H
n-C5H11



3148, 3212, 3276, 3340,
H
n-C6H13



3149, 3213, 3277, 3341,
H
n-C7H15



3150, 3214, 3278, 3342,
CH3
H



3151, 3215, 3279, 3343,
CH3
CH3



3152, 3216, 3280, 3344,
CH3
C2H5



3153, 3217, 3281, 3345,
CH3
n-C3H7



3154, 3218, 3282, 3346,
CH3
n-C4H9



3155, 3219, 3283, 3347,
CH3
n-C5H11



3156, 3220, 3284, 3348,
CH3
n-C6H13



3157, 3221, 3285, 3349,
CH3
n-C7H15



3158, 3222, 3286, 3350,
C2H5
H



3159, 3223, 3287, 3351,
C2H5
CH3



3160, 3224, 3288, 3352,
C2H5
C2H5



3161, 3225, 3289, 3353,
C2H5
n-C3H7



3162, 3226, 3290, 3354,
C2H5
n-C4H9



3163, 3227, 3291, 3355,
C2H5
n-C5H11



3164, 3228, 3292, 3356,
C2H5
n-C6H13



3165, 3229, 3293, 3357,
C2H5
n-C7H15



3166, 3230, 3294, 3358,
n-C3H7
H



3167, 3231, 3295, 3359,
n-C3H7
CH3



3168, 3232, 3296, 3360,
n-C3H7
C2H5



3169, 3233, 3297, 3361,
n-C3H7
n-C3H7



3170, 3234, 3298, 3362,
n-C3H7
n-C4H9



3171, 3235, 3299, 3363,
n-C3H7
n-C5H11



3172, 3236, 3300, 3364,
n-C3H7
n-C6H13



3173, 3237, 3301, 3365,
n-C3H7
n-C7H15



3174, 3238, 3302, 3366,
n-C4H9
H



3175, 3239, 3303, 3367,
n-C4H9
CH3



3176, 3240, 3304, 3368,
n-C4H9
C2H5



3177, 3241, 3305, 3369,
n-C4H9
n-C3H7



3178, 3242, 3306, 3370,
n-C4H9
n-C4H9



3179, 3243, 3307, 3371,
n-C4H9
n-C5H11



3180, 3244, 3308, 3372,
n-C4H9
n-C6H13



3181, 3245, 3309, 3373,
n-C4H9
n-C7H15



3182, 3246, 3310, 3374,
n-C5H11
H



3183, 3247, 3311, 3375,
n-C5H11
CH3



3184, 3248, 3312, 3376,
n-C5H11
C2H5



3185, 3249, 3313, 3377,
n-C5H11
n-C3H7



3186, 3250, 3314, 3378,
n-C5H11
n-C4H9



3187, 3251, 3315, 3379,
n-C5H11
n-C5H11



3188, 3252, 3316, 3380,
n-C5H11
n-C6H13



3189, 3253, 3317, 3381,
n-C5H11
n-C7H15



3190, 3254, 3318, 3382,
n-C6H13
H



3191, 3255, 3319, 3383,
n-C6H13
CH3



3192, 3256, 3320, 3384,
n-C6H13
C2H5



3193, 3257, 3321, 3385,
n-C6H13
n-C3H7



3194, 3258, 3322, 3386,
n-C6H13
n-C4H9



3195, 3259, 3323, 3387,
n-C6H13
n-C5H11



3196, 3260, 3324, 3388,
n-C6H13
n-C6H13



3197, 3261, 3325, 3389,
n-C6H13
n-C7H15



3198, 3262, 3326, 3390,
n-C7H15
H



3199, 3263, 3327, 3391,
n-C7H15
CH3



3200, 3264, 3328, 3392,
n-C7H15
C2H5



3201, 3265, 3329, 3393,
n-C7H15
n-C3H7



3202, 3266, 3330, 3394,
n-C7H15
n-C4H9



3203, 3267, 3331, 3395,
n-C7H15
n-C5H11



3204, 3268, 3332, 3396,
n-C7H15
n-C6H13



3205, 3269, 3333, 3397,
n-C7H15
n-C7H15










Examples 3398-3461




Examples 3462-3525




Examples 3526-3589




Examples 3590-3653
















 











Example No.
R1
R2







3398, 3462, 3526, 3590,
H
H



3399, 3463, 3527, 3591,
H
CH3



3400, 3464, 3528, 3592,
H
C2H5



3401, 3465, 3529, 3593,
H
n-C3H7



3402, 3466, 3530, 3594,
H
n-C4H9



3403, 3467, 3531, 3595,
H
n-C5H11



3404, 3468, 3532, 3596,
H
n-C6H13



3405, 3469, 3533, 3597,
H
n-C7H15



3406, 3470, 3534, 3598,
CH3
H



3407, 3471, 3535, 3599,
CH3
CH3



3408, 3472, 3536, 3600,
CH3
C2H5



3409, 3473, 3537, 3601,
CH3
n-C3H7



3410, 3474, 3538, 3602,
CH3
n-C4H9



3411, 3475, 3539, 3603,
CH3
n-C5H11



3412, 3476, 3540, 3604,
CH3
n-C6H13



3413, 3477, 3541, 3605,
CH3
n-C7H15



3414, 3478, 3542, 3606,
C2H5
H



3415, 3479, 3543, 3607,
C2H5
CH3



3416, 3480, 3544, 3608,
C2H5
C2H5



3417, 3481, 3545, 3609,
C2H5
n-C3H7



3418, 3482, 3546, 3610,
C2H5
n-C4H9



3419, 3483, 3547, 3611,
C2H5
n-C5H11



3420, 3484, 3548, 3612,
C2H5
n-C6H13



3421, 3485, 3549, 3613,
C2H5
n-C7H15



3422, 3486, 3550, 3614,
n-C3H7
H



3423, 3487, 3551, 3615,
n-C3H7
CH3



3424, 3488, 3552, 3616,
n-C3H7
C2H5



3425, 3489, 3553, 3617,
n-C3H7
n-C3H7



3426, 3490, 3554, 3618,
n-C3H7
n-C4H9



3427, 3491, 3555, 3619,
n-C3H7
n-C5H11



3428, 3492, 3556, 3620,
n-C3H7
n-C6H13



3429, 3493, 3557, 3621,
n-C3H7
n-C7H15



3430, 3494, 3558, 3622,
n-C4H9
H



3431, 3495, 3559, 3623,
n-C4H9
CH3



3432, 3496, 3560, 3624,
n-C4H9
C2H5



3433, 3497, 3561, 3625,
n-C4H9
n-C3H7



3434, 3498, 3562, 3626,
n-C4H9
n-C4H9



3435, 3499, 3563, 3627,
n-C4H9
n-C5H11



3436, 3500, 3564, 3628,
n-C4H9
n-C6H13



3437, 3501, 3565, 3629,
n-C4H9
n-C7H15



3438, 3502, 3566, 3630,
n-C5H11
H



3439, 3503, 3567, 3631,
n-C5H11
CH3



3440, 3504, 3568, 3632,
n-C5H11
C2H5



3441, 3505, 3569, 3633,
n-C5H11
n-C3H7



3442, 3506, 3570, 3634,
n-C5H11
n-C4H9



3443, 3507, 3571, 3635,
n-C5H11
n-C5H11



3444, 3508, 3572, 3636,
n-C5H11
n-C6H13



3445, 3509, 3573, 3637,
n-C5H11
n-C7H15



3446, 3510, 3574, 3638,
n-C6H13
H



3447, 3511, 3575, 3639,
n-C6H13
CH3



3448, 3512, 3576, 3640,
n-C6H13
C2H5



3449, 3513, 3577, 3641,
n-C6H13
n-C3H7



3450, 3514, 3578, 3642,
n-C6H13
n-C4H9



3451, 3515, 3579, 3643,
n-C6H13
n-C5H11



3452, 3516, 3580, 3644,
n-C6H13
n-C6H13



3453, 3517, 3581, 3645,
n-C6H13
n-C7H15



3454, 3518, 3582, 3646,
n-C7H15
H



3455, 3519, 3583, 3647,
n-C7H15
CH3



3456, 3520, 3584, 3648,
n-C7H15
C2H5



3457, 3521, 3585, 3649,
n-C7H15
n-C3H7



3458, 3522, 3586, 3650,
n-C7H15
n-C4H9



3459, 3523, 3587, 3651,
n-C7H15
n-C5H11



3460, 3524, 3588, 3652,
n-C7H15
n-C6H13



3461, 3525, 3589, 3653,
n-C7H15
n-C7H15










Examples 3654-3912
















 













Example







No.
X1
X2
R1
R2







3654,
H
H
H
CH3



3655,
H
H
H
C2H5



3656,
H
H
H
n-C3H7



3657,
H
H
H
n-C4H9



3658,
H
H
H
n-C5H11



3659,
H
H
H
n-C6H13



3660,
H
H
H
n-C7H15



3661,
F
H
H
CH3



3662,
F
H
H
C2H5



3663,
F
H
H
n-C3H7



3664,
F
H
H
n-C4H9



3665,
F
H
H
n-C5H11



3666,
F
H
H
n-C6H13



3667,
F
H
H
n-C7H15



3668,
H
F
H
CH3



3669,
H
F
H
C2H5



3670,
H
F
H
n-C3H7



3671,
H
F
H
n-C4H9



3672,
H
F
H
n-C5H11



3673,
H
F
H
n-C6H13



3674,
H
F
H
n-C7H15



3675,
F
F
H
CH3



3676,
F
F
H
C2H5



3677,
F
F
H
n-C3H7



3678,
F
F
H
n-C4H9



3679,
F
F
H
n-C5H11



3680,
F
F
H
n-C6H13



3681,
F
F
H
n-C7H15



3682,
CF3
H
H
CH3



3683,
CF3
H
H
C2H5



3684,
CF3
H
H
n-C3H7



3685,
CF3
H
H
n-C4H9



3686,
CF3
H
H
n-C5H11



3687,
CF3
H
H
n-C6H13



3688,
CF3
H
H
n-C7H15



3689,
H
CF3
H
CH3



3690,
H
CF3
H
C2H5



3691,
H
CF3
H
n-C3H7



3692,
H
CF3
H
n-C4H9



3693,
H
CF3
H
n-C5H11



3694,
H
CF3
H
n-C6H13



3695,
H
CF3
H
n-C7H15



3696,
—OCF3
H
H
CH3



3697,
—OCF3
H
H
C2H5



3698,
—OCF3
H
H
n-C3H7



3699,
—OCF3
H
H
n-C4H9



3700,
—OCF3
H
H
n-C5H11



3701,
—OCF3
H
H
n-C6H13



3702,
—OCF3
H
H
n-C7H15



3703,
H
—OCF3
H
CH3



3704,
H
—OCF3
H
C2H5



3705,
H
—OCF3
H
n-C3H7



3706,
H
—OCF3
H
n-C4H9



3707,
H
—OCF3
H
n-C5H11



3708,
H
—OCF3
H
n-C6H13



3709,
H
—OCF3
H
n-C7H15



3710,
H
H
CH3
CH3



3711,
H
H
CH3
C2H5



3712,
H
H
CH3
n-C3H7



3713,
H
H
CH3
n-C4H9



3714,
H
H
CH3
n-C5H11



3715,
H
H
CH3
n-C6H13



3716,
H
H
CH3
n-C7H15



3717,
F
H
CH3
CH3



3718,
F
H
CH3
C2H5



3719,
F
H
CH3
n-C3H7



3720,
F
H
CH3
n-C4H9



3721,
F
H
CH3
n-C5H11



3722,
F
H
CH3
n-C6H13



3723,
F
H
CH3
n-C7H15



3724,
F
F
CH3
CH3



3725,
F
F
CH3
C2H5



3726,
F
F
CH3
n-C3H7



3727,
F
F
CH3
n-C4H9



3728,
F
F
CH3
n-C5H11



3729,
F
F
CH3
n-C6H13



3730,
F
F
CH3
n-C7H15



3731,
CF3
H
CH3
CH3



3732,
CF3
H
CH3
C2H5



3733,
CF3
H
CH3
n-C3H7



3734,
CF3
H
CH3
n-C4H9



3735,
CF3
H
CH3
n-C5H11



3736,
CF3
H
CH3
n-C6H13



3737,
CF3
H
CH3
n-C7H15



3738,
—OCF3
H
CH3
CH3



3739,
—OCF3
H
CH3
C2H5



3740,
—OCF3
H
CH3
n-C3H7



3741,
—OCF3
H
CH3
n-C4H9



3742,
—OCF3
H
CH3
n-C5H11



3743,
—OCF3
H
CH3
n-C6H13



3744,
—OCF3
H
CH3
n-C7H15



3745,
H
H
C2H5
C2H5



3746,
H
H
C2H5
n-C3H7



3747,
H
H
C2H5
n-C4H9



3748,
H
H
C2H5
n-C5H11



3749,
H
H
C2H5
n-C6H13



3750,
H
H
C2H5
n-C7H15



3751,
F
H
C2H5
CH3



3752,
F
H
C2H5
C2H5



3753,
F
H
C2H5
n-C3H7



3754,
F
H
C2H5
n-C4H9



3755,
F
H
C2H5
n-C5H11



3756,
F
H
C2H5
n-C6H13



3757,
F
H
C2H5
n-C7H15



3758,
F
F
C2H5
C2H5



3759,
F
F
C2H5
n-C3H7



3760,
F
F
C2H5
n-C4H9



3761,
F
F
C2H5
n-C5H11



3762,
F
F
C2H5
n-C6H13



3763,
F
F
C2H5
n-C7H15



3764,
CF3
H
C2H5
CH3



3765,
CF3
H
C2H5
C2H5



3766,
CF3
H
C2H5
n-C3H7



3767,
CF3
H
C2H5
n-C4H9



3768,
CF3
H
C2H5
n-C5H11



3769,
CF3
H
C2H5
n-C6H13



3770,
CF3
H
C2H5
n-C7H15



3771,
—OCF3
H
C2H5
CH3



3772,
—OCF3
H
C2H5
C2H5



3773,
—OCF3
H
C2H5
n-C3H7



3774,
—OCF3
H
C2H5
n-C4H9



3775,
—OCF3
H
C2H5
n-C5H11



3776,
—OCF3
H
C2H5
n-C6H13



3777,
—OCF3
H
C2H5
n-C7H15



3778,
H
H
n-C3H7
n-C3H7



3779,
H
H
n-C3H7
n-C4H9



3780,
H
H
n-C3H7
n-C5H11



3781,
H
H
n-C3H7
n-C6H13



3782,
H
H
n-C3H7
n-C7H15



3783,
F
H
n-C3H7
CH3



3784,
F
H
n-C3H7
C2H5



3785,
F
H
n-C3H7
n-C3H7



3786,
F
H
n-C3H7
n-C4H9



3787,
F
H
n-C3H7
n-C5H11



3788,
F
H
n-C3H7
n-C6H13



3789,
F
H
n-C3H7
n-C7H15



3790,
F
F
n-C3H7
n-C3H7



3791,
F
F
n-C3H7
n-C4H9



3792,
F
F
n-C3H7
n-C5H11



3793,
F
F
n-C3H7
n-C6H13



3794,
F
F
n-C3H7
n-C7H15



3795,
CF3
H
n-C3H7
CH3



3796,
CF3
H
n-C3H7
C2H5



3797,
CF3
H
n-C3H7
n-C3H7



3798,
CF3
H
n-C3H7
n-C4H9



3799,
CF3
H
n-C3H7
n-C5H11



3800,
CF3
H
n-C3H7
n-C6H13



3801,
CF3
H
n-C3H7
n-C7H15



3802,
—OCF3
H
n-C3H7
CH3



3803,
—OCF3
H
n-C3H7
C2H5



3804,
—OCF3
H
n-C3H7
n-C3H7



3805,
—OCF3
H
n-C3H7
n-C4H9



3806,
—OCF3
H
n-C3H7
n-C5H11



3807,
—OCF3
H
n-C3H7
n-C6H13



3808,
—OCF3
H
n-C3H7
n-C7H15



3809,
H
H
n-C4H9
n-C4H9



3810,
H
H
n-C4H9
n-C5H11



3811,
H
H
n-C4H9
n-C6H13



3812,
H
H
n-C4H9
n-C7H15



3813,
F
H
n-C4H9
CH3



3814,
F
H
n-C4H9
C2H5



3815,
F
H
n-C4H9
n-C3H7



3816,
F
H
n-C4H9
n-C4H9



3817,
F
H
n-C4H9
n-C5H11



3818,
F
H
n-C4H9
n-C6H13



3819,
F
H
n-C4H9
n-C7H15



3820,
F
F
n-C4H9
n-C4H9



3821,
F
F
n-C4H9
n-C5H11



3822,
F
F
n-C4H9
n-C6H13



3823,
F
F
n-C4H9
n-C7H15



3824,
CF3
H
n-C4H9
CH3



3825,
CF3
H
n-C4H9
C2H5



3826,
CF3
H
n-C4H9
n-C3H7



3827,
CF3
H
n-C4H9
n-C4H9



3828,
CF3
H
n-C4H9
n-C5H11



3829,
CF3
H
n-C4H9
n-C6H13



3830,
CF3
H
n-C4H9
n-C7H15



3831,
—OCF3
H
n-C4H9
CH3



3832,
—OCF3
H
n-C4H9
C2H5



3833,
—OCF3
H
n-C4H9
n-C3H7



3834,
—OCF3
H
n-C4H9
n-C4H9



3835,
—OCF3
H
n-C4H9
n-C5H11



3836,
—OCF3
H
n-C4H9
n-C6H13



3837,
—OCF3
H
n-C4H9
n-C7H15



3838,
H
H
n-C5H11
n-C5H11



3839,
H
H
n-C5H11
n-C6H13



3840,
H
H
n-C5H11
n-C7H15



3841,
F
H
n-C5H11
CH3



3842,
F
H
n-C5H11
C2H5



3843,
F
H
n-C5H11
n-C3H7



3844,
F
H
n-C5H11
n-C4H9



3845,
F
H
n-C5H11
n-C5H11



3846,
F
H
n-C5H11
n-C6H13



3847,
F
H
n-C5H11
n-C7H15



3848,
F
F
n-C5H11
n-C5H11



3849,
F
F
n-C5H11
n-C6H13



3850,
F
F
n-C5H11
n-C7H15



3851,
CF3
H
n-C5H11
CH3



3852,
CF3
H
n-C5H11
C2H5



3853,
CF3
H
n-C5H11
n-C3H7



3854,
CF3
H
n-C5H11
n-C4H9



3855,
CF3
H
n-C5H11
n-C5H11



3856,
CF3
H
n-C5H11
n-C6H13



3857,
CF3
H
n-C5H11
n-C7H15



3858,
—OCF3
H
n-C5H11
CH3



3859,
—OCF3
H
n-C5H11
C2H5



3860,
—OCF3
H
n-C5H11
n-C3H7



3861,
—OCF3
H
n-C5H11
n-C4H9



3862,
—OCF3
H
n-C5H11
n-C5H11



3863,
—OCF3
H
n-C5H11
n-C6H13



3864,
—OCF3
H
n-C5H11
n-C7H15



3865,
H
H
n-C6H13
n-C6H13



3866,
H
H
n-C6H13
n-C7H15



3867,
F
H
n-C6H13
CH3



3868,
F
H
n-C6H13
C2H5



3869,
F
H
n-C6H13
n-C3H7



3870,
F
H
n-C6H13
n-C4H9



3871,
F
H
n-C6H13
n-C5H11



3872,
F
H
n-C6H13
n-C6H13



3873,
F
H
n-C6H13
n-C7H15



3874,
F
F
n-C6H13
n-C6H13



3875,
F
F
n-C6H13
n-C7H15



3876,
CF3
H
n-C6H13
CH3



3877,
CF3
H
n-C6H13
C2H5



3878,
CF3
H
n-C6H13
n-C3H7



3879,
CF3
H
n-C6H13
n-C4H9



3880,
CF3
H
n-C6H13
n-C5H11



3881,
CF3
H
n-C6H13
n-C6H13



3882,
CF3
H
n-C6H13
n-C7H15



3883,
—OCF3
H
n-C6H13
CH3



3884,
—OCF3
H
n-C6H13
C2H5



3885,
—OCF3
H
n-C6H13
n-C3H7



3886,
—OCF3
H
n-C6H13
n-C4H9



3887,
—OCF3
H
n-C6H13
n-C5H11



3888,
—OCF3
H
n-C6H13
n-C6H13



3889,
—OCF3
H
n-C6H13
n-C7H15



3890,
H
H
n-C7H15
n-C7H15



3891,
F
H
n-C7H15
CH3



3892,
F
H
n-C7H15
C2H5



3893,
F
H
n-C7H15
n-C3H7



3894,
F
H
n-C7H15
n-C4H9



3895,
F
H
n-C7H15
n-C5H11



3896,
F
H
n-C7H15
n-C6H13



3897,
F
H
n-C7H15
n-C7H15



3898,
F
F
n-C7H15
n-C7H15



3899,
CF3
H
n-C7H15
CH3



3900,
CF3
H
n-C7H15
C2H5



3901,
CF3
H
n-C7H15
n-C3H7



3902,
CF3
H
n-C7H15
n-C4H9



3903,
CF3
H
n-C7H15
n-C5H11



3904,
CF3
H
n-C7H15
n-C6H13



3905,
CF3
H
n-C7H15
n-C7H15



3906,
—OCF3
H
n-C7H15
CH3



3907,
—OCF3
H
n-C7H15
C2H5



3908,
—OCF3
H
n-C7H15
n-C3H7



3909,
—OCF3
H
n-C7H15
n-C4H9



3910,
—OCF3
H
n-C7H15
n-C5H11



3911,
—OCF3
H
n-C7H15
n-C6H13



3912,
—OCF3
H
n-C7H15
n-C7H15

















TABLE 1







Δε and Δn values for substances of individual examples









Example




No.
Δε
Δn












73
-10.2
0.006


106
-10.3
0.068


137
-10.0
0.069


1401
-6.8
0.074


1402
-7.4
0.072


2325
-8.7
0.078


3726
-4.4
0.087


3758
-5.0
0.088


3759
-4.5
0.088


3790
-4.4
0.088

## Claims

1. A compound of formula I:




in which:




independently of one another, stand for



A1 and A2 are each, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O —or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
Z1 and Z2 are each, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
R1 and R2 are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted, monosubstituted by —CN or —CF3 or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF5; 
m and n, independently of one another, are 0, 1, 2 or 3;
X1, X2 and Y2 are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS;
Y1 is hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS, or
Y1 is —[—Z3—A3—]p-—R3;
Z3 is a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
A3 is 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2 may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
R3 is hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted, monosubstituted by —CN or —CF3 or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF5; and
p is 0, 1,2 or 3;

where
A1,A2,A3,Z1,Z2,Z3,R2,R2 and R3 may each have identical or different meanings if m, n and p respectively are greater than 1;
Y1 and Y2 may each have identical or different meanings for rings B and B′;

and where
(a) R1-[-A1-Z1-]m- and -[-Z2-A2-]n-R2 are not simultaneously CH3 if one of X1 and X2 is hydrogen and the other of X1 and X2 is Cl and at the same time both rings B and B′ stand for ring g; and
(b) at least one X1, X2, Y1 or Y2 group is F, Cl, CF3, or OCF3.

2. A compound according to claim 1, wherein rings B and B′ are identical, Y1 in both rings can have identical or different meanings, and Y2 in both rings can have identical or different meanings.

3. A compound according to claim 1, wherein said compound is selected from formulae Iaa, Ibb, Iee, Iff and Igg:




where Y11 Y12 can have identical or different meanings and are each hydrogen, -[-Z3-A3-]p-R3, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN, or —NCS; and
Y21 and Y22 can have identical or different meanings and are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS.

4. A compound according to claim 1, wherein Y1 and Y2 are simultaneously F.

5. A compound according to claim 1, wherein Z1, Z2, and Z3, if present, independently of one another, are each a single bond, —CF2O—, —OCF2—, —CF2CF2—, —CH═CH—, —CF═CH—, —CH═CF —or -CF═CF—.

6. A compound according to claim 1, wherein A1, A2, and A3, if present, independently of one another, are each

7. A compound according to claim 1, wherein R1, R2, and R3, if present, independently of one another, are each alkanyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms, or alkenyl radical having 2 to 7 C atoms.

8. A compound according to claim 1, wherein
m is 0, 1 or 2;
n is 0, 1 or 2;
m+n is 0, 1, 2 or 3; and
p is 0.

9. A compound according to claim 1, wherein at least one of X1 and X2 is F, Cl, CF3 or OCF3.

10. A compound according to claim 1, wherein X1 and X2 are F.

11. A liquid-crystalline medium comprising at least two liquid-crystalline compounds, wherein said medium comprises at least one compound according to claim 1.

12. An electro-optical display element containing a liquid-crystalline medium according to claim 1.

13. A compound according to claim 3, wherein Y11, Y12, Y21 and Y22 are simultaneously F.

14. A compound of formula I:




in which:




independently of one another, stand for



A1 and A2 are each, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2- may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
Z1 and Z2 are each, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
R1 and R2 independently of one another, are each alkanyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms, or alkenyl radical having 2 to 7 C atoms;
m and n, independently of one another, are 0, 1, 2 or 3, and n+m is 1, 2, or 3;
X1, X2 and Y2 are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —-O—, —-S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS;
Y1 is hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS, or
Y1 is -[-Z3 -A3-]p-R3;
Z3 is a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
A3 is 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
R3 is alkanyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms, or alkenyl radical having 2 to 7 C atoms; and
p is 0, 1, 2 or 3;

where
A1, A2, A3, Z1, Z2, Z3, R1, R2 and R3 may each have identical or different meanings if m, n and p respectively are greater than 1;
Y1 and Y2 may each have identical or different meanings for rings B and B′;

and where
(a) R1 does not stand for —COOH if ring B stands for ring f or g and ring B′ stands for ring d and at the same time m is zero and X2 is not H, or R2 does not stand for —COOH if ring B′ stands for ring f or g and ring B stands for ring d and n is zero and X1 is not H;
(b) R1-[-A1-Z1-]m- and -[-Z2-A2-]n-R2 are not simultaneously CH3 if one of X1 and X2 is hydrogen and the other of X1 and X2 hydrogen or Cl and at the same time both rings B and B′ stand for ring g.

15. A liquid-crystalline medium comprising at least two liquid-crystalline compounds, wherein said medium comprises at least one compound according to formula I:




in which:




independently of one another, stand for



A1 and A2 are each, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O—or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
Z1 and Z2 are each, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
R1 and R2 are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted, monosubstituted by —CN or —CF3 or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO—or —OCO—O—in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF5;
m and n, independently of one another, are 0, 1, 2 or 3;
X1, X2 and Y2 are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCOO— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS;
Y1 is hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS, or
Y1 is -[-Z3 -A3-]p-R3;
Z3 is a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
A3 is 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N—and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6- alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
R3 is hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted, monosubstituted by —CN or —CF3 or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO—or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF5; and
p is 0, 1, 2 or 3;

where
A1,A2,A3, Z1, Z2, Z3, R1, R2 and R3 may each have identical or different meanings if m, n and p respectively are greater than 1;
Y1 and Y2 may each have identical or different meanings for rings B and B′;

and where
(a) R1 does not stand for —COOH if ring B stands for ring f or g and ring B′ stands for ring d and at the same time m is zero and X2 is not H, or
R2 does not stand for —COOH if ring B′ stands for ring f or g and ring B stands for ring d and n is zero and X1 is not H;
(b) R1-[-A1-Z1-]m- and -[-Z2-A2 -]n-R2 are not simultaneously CH3 if one of X1 and X2 is hydrogen and the other of X1 and X2 hydrogen or Cl and at the same time both rings B and B′ stand for ring g.

16. An electro-optical display element containing a liquid-crystalline medium according to at least one compound according to formula I:




in which:




independently of one another, stand for



A1 and A2 are each, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2- may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
Z1 and Z2 are each, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
R1 and R2 are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted, monosubstituted by —CN or —CF3 or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF5;
m and n, independently of one another, are 0, 1, 2 or 3;
X1, X2 and Y2 are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS;
Y1 is hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS, or
Y1 is -[-Z3-A3-]p-R3;
Z3 is a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
A3 is 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2- may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
R3 is hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted, monosubstituted by —CN or —CF3 or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF5; and
p is 0, 1, 2 or 3;

where
A1, A2, A3, Z1, Z2, Z3, R1, R2 and R3 may each have identical or different meanings if m, n and p respectively are greater than 1;
Y1 and Y2 may each have identical or different meanings for rings B and B′;

and where
(a) R1 does not stand for —COOH if ring B stands for ring f or g and ring B′ stands for ring d and at the same time m is zero and X2 is not H, or R2 does not stand for -COOH if ring B′ stands for ring f or g and ring B stands for ring d and n is zero and X1 is not H;
(b) R1-[-A1-Z1-]m- and -[-Z2-A2-]n-R2 are not simultaneously CH3 if one of X1 and X2 is hydrogen and the other of X1 and X2 is hydrogen or Cl and at the same time both rings B and B′ stand for ring g.

17. A compound according to claim 1, wherein said compound has a dielectric anisotropy Δε of <-2.

18. A compound according to claim 1, wherein said compound has a dielectric anisotropy Δε of <-5.

19. A compound according to claim 1, wherein said compound has an optical anisotropy Δn of greater than 0.02 and less than 0.25.

20. A compound according to claim 1, wherein at least one of X21 and Xis other than hydrogen.

21. A compound according to claim 3, wherein Y11, Y12, Y21 and Y22 are, independently of one another, H, F, Cl or a (per)fluorinated alkanyl or alkoxy radical having up to 6 carbon atoms.

22. A compound according to claim 3, wherein Z1 and Z2 and, if present Z3, are each independently of one another, a single bond, —CF2O—, —OCF2—,—CF2CF2—, —CH═CH—, —CF═CH—, —CH═CF— or —CF═CF.

23. A compound according to claim 1, wherein R1, R2, R3, X1, X2, Y1 and Y2 are each, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, 2-oxa-propyl, 2- or 3-oxabutyl, 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl, acetoxy, propionyloxy, butyryloxy, pentanoyloxy, hexanoyloxy, acetoxymethyl, propionyloxymethyl, butyryloxymethyl, pentanoyloxymethyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-acetoxy-propyl, 3 -propionyloxypropyl, 4-acetoxybutyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, butoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 3 -(ethoxycarbonyl)propyl, 4-(methoxycarbonyl)butyl, acryloyloxymethyl, 2-acryloyloxyethyl, 3-acryloyloxypropyl, 4-acryloyloxybutyl, 5-acryloyloxypentyl, 6-acryloyloxyhexyl, 7-acryloyloxyheptyl, 8-acryloyloxyoctyl, 9-acryloyl-oxynonyl, methacryloyloxymethyl, 2-methacryloyloxyethyl, 3-methacryloyloxypropyl, 4-methacryloyloxybutyl, 5-methacryloyloxypentyl, 6-methacryloyloxyhexyl, 7-methacryloyloxyheptyl, 8-methacryloyloxyoctyl, —CF3, F, —Cl, —Br, —I, —CN, —SCN, —NCS or —SF5. 1 2

24. A compound according to claim 1, wherein R1, R2 and R3, if present, are, independently of one another, alkanyl having 1 to 7, alkoxy having 1 to 7, or alkenyl having 2 to 7 C atoms.

25. A compound according to claim 1, wherein X1 and X2 are, independently of one another, hydrogen, halogen, or alkanyl having 1 to 7, alkoxy having 1 to 7, or alkenyl having 2 to 7 C atoms respectively, each of which is at least monosubstituted by halogen.

26. A compound according to claim 25, wherein at least one of X1 and X2 is —CF3, —OCF3, F or Cl.

27. A compound according to claim 1, wherein n+m is 0 or 1.

28. A display according to claim 12, wherein said compound is in a liquid-crystalline layer having a thickness of 5 to 10 μm, said layer is arranged between two plane-parallel glass plates, onto each of which an electrically conductive, transparent layer of tin oxide or indium tin oxide is provided as an electrode, and a transparent alignment layer is positioned between the electrodes and the liquid-crystalline layer.

29. A display according to claim 16, wherein said compound is in a liquid-crystalline layer having a thickness of 5 to 10 μm, said layer is arranged between two plane-parallel glass plates, onto each of which an electrically conductive, transparent layer of tin oxide or indium tin oxide is provided as an electrode, and a transparent alignment layer is positioned between the electrodes and the liquid-crystalline layer.

30. A compound according to claim 1, wherein said compound is selected from formulae Iaa, Iaf, and Iag:




where
Y11 and Y12 can have identical or different meanings and are each hydrogen, -[-Z3-A3-]p-R3, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN, or —NCS; and
Y21 and Y22 can have identical or different meanings and are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O——, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS.

31. A compound according to claim 1, wherein said compound is selected from formulae Iba, Iaf, and Iag:




where
Y11 and Y12 can have identical or different meanings and are each hydrogen, -[-Z3-A3-]p-R3, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN, or —NCS; and
Y21 and Y22 can have identical or different meanings and are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS.

32. A compound of formula I:




in which:




independently of one another, stand for



A1 and A2 are each, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
Z1 and Z2 are each, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
R1 and R2 are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted, monosubstituted by —CN or —CF3 or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF5;
m and n, independently of one another, are 0, 1, 2 or 3;
X1, X2 and Y2 are each, independently of one another, hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O—O in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS;
Y1 is hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF5, —SCN or —NCS, or
Y1 is -[-Z3-A3-]p-R3;
Z3 is a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;
A3 is 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C1-C6-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C1-C6-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2- may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I;
R3 is hydrogen, or alkanyl having 1 to 15 C atoms, alkoxy having 1 to 15 C atoms, alkenyl having 2 to 15 C atoms, or alkynyl having 2 to 15 C atoms, each of which is unsubstituted, monosubstituted by —CN or —CF3 or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF5; and
p is 0, 1, 2 or 3;

where
A1, A2, A3, Z1, Z2, Z3, R1, R2 and R3 may each have identical or different meanings if m, n and p respectively are greater than 1;
Y1 and Y2 may each have identical or different meanings for rings B and B′;

and where
(a) R1-[-A1-Z1-]m and -[-Z2-A2-]n-R2 are not simultaneously CH3 if one of X1 and X2 is hydrogen and the other of X1 and X2 Cl and at the same time both rings B and B′ stand for ring g; and
(b) at least one X1, X2, Y1 or Y2 group is F, Cl, CF3, or OCF3.

33. A compound according to claim 14, wherein m is 1 and n is 0.