bluuebunny/crossref_metadata_2025_split huggingface dataset:
The reaction between tri‐n‐octylamine and sulfuric acid
Authors: Foppema R. 
Published: September 2010

AbstractA kinetical study is reported on the reaction between aqueous sulfuric acid and 0.4 to 1.0 M solutions of tri‐n‐octylamine (TOA) in chloroform. The results are interpreted in terms of a reaction mechanism in which two types of the intermediate TOAH+ ion are distinguished. The proposed mechanism accounts for form and magnitude of the observed equilibrium constant

A hypothetical explanation is offered for the distinction between the two intermediates. The hypothesis predicts that below a critical sulfate ion activity interconversion of the intermediates becomes predominant, leading to a more simple mechanism and a more conventional form of the equilibrium constant. Such a transition could be responsible for earlier observations, where a different type of equilibrium constant with a limited validity area was found for the analogous reaction with benzene solutions of the amine.
Photodehydrocyclizations in stilbene‐like compounds
Authors: Laarhoven W. H. , Cuppen Th. J. H. M. , Nivard R. J. F. 
Published: September 2010

AbstractPhotodehydrocyclizations, analogous to the formation of phenanthrene from stilbene, appear to be possible only if the sum of the free valence numbers of the proper atoms in the first excited state exceeds a critical value. Localization energies and superdelocalizabilities also set bounds to the occurrence of this type of reaction. Calculation of the relative magnitudes by the simple Hückel MO method appears to be satisfactory only in alternating compounds.
Factors governing cyclopropane versus pyrazoline formation in the reaction of diazomethane with s‐trinitrobenzene: Nucleophilic aromatic addition VIII
Authors: Louwrier‐De Wal J. , de Boer Th. J. 
Published: September 2010

Abstractsym‐Trinitrobenzene reacts successively with three molecules of diazomethane yielding “trismethylene‐trinitrobenzene” (VIII). In each stage an intermediate diazonium betaine (II, V and VII) is postulated with considerable negative charge delocalisation. Such betaines lose nitrogen to give cyclopropanes rather than retaining nitrogen with ring closure to give pyrazolines. Pyrazoline formation becomes important when charge delocalisation is restricted, as in the reaction of the non‐conjugated double bond in VIII with a (fourth) molecule of diazomethane yielding the stable pyrazoline IX either via a betaine or by 1,3‐dipolar addition.
HF‐SbF5 catalysed isomerization of 2‐methylpentane: Kinetics and mechanism of rearrangement and hydride‐ion transfer steps in alkylcarbonium ion reactions
Authors: Brouwer D. M. , Oelderik J. M. 
Published: September 2010

AbstractA kinetic investigation has been made of the isomerization of 2‐methylpentane with liquid HF‐SbF5 as catalyst at temperatures of from −20 to +20 °C. The isomerization proceeds in three distinct stages: first 3‐methylpentane is formed, then the equilibrium mixture of 2‐ and 3‐methylpentane isomerizes to equilibrium with 2,3‐dimethylbutane, and finally that mixture reacts to give n‐hexane and neohexane, respectively, until thermodynamic equilibrium is reached. Rate constants at 0 ° for these four reactions are 0.42, 0.030, 0.00015, and 0.0007 s−1 · (mole hexane) · (mole SbF5)−1, respectively. In the first reaction, mass transfer between acid and hydrocarbon phases is rate limiting; the rate‐determining step of the second reaction is the intramolecular rearrangement of the intermediate tertiary carbonium ions, and of the last two reactions the intermolecular hydride‐ion transfer between secondary and tertiary carbons. The rate constant for hydrideion transfer from a secondary carbon to a tertiary carbonium ion is about 0.06 1 · mole−1 · s−1 at 0 ° (EA = 14−15 kcal · mole−1), and for that between two tertiary carbons is greater than 10 1 · mole−1 · s−1. The rate of rearrangement of a tertiary ion to a secondary or tertiary ion with different degree of chain branching is about 0.1 s−1 at 0 ° (EA = 16−17 kcal · mole−1). A mechanism for that type of rearrangement via a (protonated) cyclopropane ring is consistent with the data. In particular, it explains why n‐butane does not isomerize to isobutane under conditions where n‐pentane and n‐hexane are rapidly converted.
Complexes with ligands containing nitrile groups: Part IV. Systems of di‐ and tri‐valent metal chlorides with antimony pentachloride in methyl cyanide
Authors: Zuur A. P. , van Houte J. J. , Groeneveld W. L. 
Published: September 2010

AbstractConductometric as well as potentiometric tritrations are reported to study the Cl−ion transfer in systems consisting of di‐ and tri‐valent metal chlorides with antimony pentachloride in methyl cyanide.On the basis of the potentiometric titrations a theoretical discussion is given of this Cl− ion transfer.During the potentiometric measurements it was ascertained that chlorinated molybdenum metal can be used as a reversible secondary chlorine electrode.In the solid state several complexes of the types:M3+(CH3CN)x · (SbCl6−)3 in which M = Al3+, Ga3+, In3+, Cr3+, V3+ and La3+, MCl2+(CH3CN)y · (SbCl6−)2 in which M = Fe3+ and MCl2+1(CH3CN)z · (SbCl6−) in which M = B3+, Tl3+ and Bi3+ are reported.The formation of these complexes is studied using ternary phase diagrams.
The synthesis of some bis(1‐substituted cyclohexyl) nitroxides
Authors: Duynstee E. F. J. , Mevis M. E. A. H. , Ostendorf H. K. , de Kock R. J. 
Published: September 2010

AbstractThe nitrile and several esters of 1‐nitrosocyclohexanecarboxylic acid all gave the expected nitroxides upon thermal decomposition in toluene. These bis(1‐substituted cyclohexyl) nitroxides could not be isolated from the decomposition product and were therefore prepared in the pure form by another route, involving peracid‐oxidation of the corresponding bis(1‐substituted cyclohexyl) amines. The nitroxides were stable in the solid state, but in solution a slow decomposition occurred. Hydrogenation of the nitroxides yielded the corresponding hydroxylamines. The ESR parameters of the nitroxides are given.
Properties of diazosulfonates. Part VI: Quantum yields for the photolysis of 2‐methoxybenzenediazonium and for the photo‐isomerization of 2‐methoxybenzene‐trans‐diazosulfonate
Authors: Jonker H. , Thijssens Th. P. G. W. , van Beek L. K. H. 
Published: September 2010

AbstractQuantum yields at pH = 1 and 4 were determined at 254, 313, 366 and 436 nm with the potassium ferrioxalate actinometer. The photoreactions were interpreted considering the reactions trans diazonium + sulfite, followed by photolysis of diazonium ions. The quantum yields for the photolysis of diazonium ions at 20° are 0.56 (254 nm), 0.39 (313 nm) and those for the photo‐isomerization of trans‐diazosulfonate are 0.29 (254 nm), 0.32 (313 nm), 0.37 (366 nm) and 0.42 (436 nm).The trans‐cis isomerization constant Kf = ke/kt = 2.7 × 10−5 and the dissociation constant of the cis isomer Ke = k1/k2 = 1.8 × 10−5 mole/1 were derived from irradiation experiments at 436 nm and at pH = 7. The rate constants at 20° corrected to zero ionic strength are ke = 3.5 × 10−7S−1, kt = k1 = 0.013 s−1, and k2 = 700 1/mole. s.
Complexes of ligands containing S=O. Part VI. Metal‐ligand vibrations in complexes of tetramethylene sulfoxide
Authors: Reedijk J. , van Leeuwen P. W. N. M. , Groeneveld W. L. 
Published: September 2010

AbstractInfrared spectra in the region 600‐200 cm−1 have been recorded for a number of complexes having the general formula M(C4H8SO)m(ClO4)n, in which M = Mg(II), Al(III), Ca(II), Cr(III), Mn(II), Fe(III), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II); m = 4 or 6; n = 2 or 3.The band assigned to the vibration being mainly metal‐oxygen occurs in the region 370‐500 cm−1 for all the complexes studied. The frequency order for the divalent transition‐metal ions is found to be: Mn < Zn < Fe < Co < Ni < Cu, in agreement with other sequences and with the general stability order of Irving and Williams.
Some conversions of allenyl ethers
Authors: Hoff S. , Brandsma L. , Arens J. F. 
Published: September 2010

AbstractMetallation of methoxypropadiene, CH2 = C = CHOCH3, with butyllithium in ether, followed by reaction with carbonyl compounds, R1R2C = O (R1 and R2 = H or alkyl or R1R2C = cyclohexyl), affords carbinols, CH2 = C = C[CR1R2 (OH)]OCH3, in excellent yields. Acid‐catalysed hydrolysis of these carbinols gives nearly quantitative yields of unsaturated ketols, magnified image 1‐Methoxy‐1‐methylthiopropadiene, CH2 = C = C(OCH3) (SCH3) (VI), has been obtained in 75% yield by adding CH3SSCH3 to the lithiated allenyl ether. Acid‐catalysed addition of alcohols, ROH (R = CH3 or C2H5), to methoxypropadiene affords acrolein acetals, CH2 = CHCH(OCH3) (OR) (VII), in good yields.Diels‐Alder addition of ethoxypropadiene to a,β‐unsaturated aldehydes, R3CH = CH ‐ CH = O (R3 = H or CH3), leads to derivatives of 2,3‐dihydropyran (VIII).The yields are moderate.magnified image
The kinetics and thermochemistry of the thermal rearrangement of hexamethylbicyclo[2.2.0]hexa‐2,5‐diene (hexamethyldewarbenzene) and of hexamethyltetracyclo[2.2.0,02,6.03,5]hexane (hexamethylprismane)
Authors: Oth Jean F. M. 
Published: September 2010

AbstractHexamethylbicyclo[2.2.0]hexa‐2,5‐diene (hexamethyldewarbenzene) (II) rearranges thermally into hexamethylbenzene (III) above 80°. The kinetic parameters and the heat of this reaction were measured. From the heat of the reaction, from the heat of combustion of III and using thermochemical data, the strain energy of II could be deduced as:

Hexamethyltetracyclo[2.2.0.02,6.03,5]hexane (hexamethylprismane) (I) rearranges thermally into hexamethylbenzene (III). Kinetic experiments have shown that the rearrangement I → III proceeds along two parallel paths: ‐ in one path the rearrangement goes via hexamethyldewarbenzene (II) which accumulates appreciable in the course of the reaction; ‐ in one other path, the rearrangement goes most likely via hexamethyl‐tricyclo[2.1.1.05,6]hex‐2‐ene (hexamethylbenzvalene) (IV).The kinetic parameters of the different steps and the overall heat of isomerization I → III were measured. From the heat of isomerization I → III, the strain energy of hexamethylprismane (I) could be deduced as:
Solid‐Phase synthesis of carboxyl‐terminal N‐substituted derivatives of oxytocin
Authors: Beyerman H. C. , van den Brink‐Zimmermannová H. Maassen 
Published: September 2010

AbstractPreviously we described the synthesis of N‐benzyloxycarbonyl‐S,S′‐dibenzyloxytocinoic acid on copolystyrene‐divinylbenzene according to the solid‐phase method of Merrifield, but using the triazolide coupling developed in this Laboratory. The nonapeptide‐polymer bond could be cleaved quite satisfactorily with methanolic ammonia to yield the linear peptide corresponding to oxytocin. Cyclization to the hormone oxytocin was known.We now describe the facile cleavage of the nonapeptide‐polymer bond with methylamine, with hydroxylamine, and with hydrazine, which yielded the linear peptides corresponding to N‐benzyloxycarbonyl‐S,S′‐dibenzyloxytocinoic acid N′‐methylamide, N′‐hydroxyamide, and hydrazide, respectively.Cyclization of the first derivative, presumably to oxytocinoic acid N′‐methylamide, gave material without appreciable avian depressor (fowl) activity.
Chemistry and spectroscopy in strongly acidic solutions. Part XIX: Behaviour of α,α‐dimethyl‐β‐propiolactone and hydroxypivalic acid in hydrogen fluoride‐boron trifluoride solution
Authors: Hogeveen H. 
Published: September 2010

AbstractWhen α,α‐dimethyl‐β‐propiolactone is dissolved in HF‐BF3 solution at −80° C, an acyl‐oxygen cleavage of the ring occurs which results in the formation of protonated hydroxymethyldimethylacetyl cation (I). The hydrated form of this dication, dication (II), is obtained by protonation of hydroxypivalic acid under the same conditions.Heating of a solution of (I) in HF‐BF3 to about −40° modifies the NMR spectrum reversibly owing to a rapid deprotonation. At about 0° an irreversible reaction takes place with the formation of oligomers (IV). At room temperature (IV) is irreversibly transformed into unsaturated oligomers (VI). Additional information on the products has been obtained from NMR, IR and mass spectrometric data of the compounds formed on quenching the acidic solutions with water.Warming up of ion (II) to 10° effects dehydration to ion (I) and subsequent formation of oligomers (IV).
Photoreactions of aromatic compounds. Part XIV: The mechanism of the photosolvolysis of m‐nitrophenyl phosphate
Authors: de Jongh R. O. , Havinga E. 
Published: September 2010

AbstractQuantum yields (φ) of photosolvolysis of m‐nitrophenyl phosphate have been determined at various hydroxyl ion concentrations and ionic strengths. The values obtained are practically the same (slightly lower) when light of 265 mμ is used as compared with those at 313 mμ, indicating that photochemical processes do not start directly from the second excited singlet, φ is independent of pH and ionic strength in neutral or weakly alkaline media (φ = 0.05 up to pH = 10‐11), suggesting that here H2O is the attacking reagent. At pH = 12 and higher there is an increase of φ with increasing [OH−] as well as with increasing ionic strength. Most probably here ‐ superimposed upon the reaction with H2O ‐, an attack by OH− takes place. The data are consistent with a simple tentative scheme (Fig. 1). 18O‐experiments indicate that water attacks at phosphorus (OP splitting) whereas OH− attacks at the ring carbon atom (CO splitting).With o‐nitrophenyl phosphate and p‐nitrophenyl phosphate the quantum yields (in 0.01 molar NaOH) for phosphate liberation are 0.003 and 0.002, respectively; the values for nitrophenolate formation are still lower: 0.002 and 0.0004. Not only are the rates of solvolysis of the ortho‐ and para‐isomers much smaller than that of the meta compound (0.055) but also the overall reactions seem to be more complex.
Carbon‐13 nuclear magnetic resonance of some acetylenic compounds
Authors: Rosenberg D. , Drenth W. , de Haan J. W. 
Published: September 2010

Abstract13C nuclear magnetic resonances were measured for heterosubstituted acetylenes. The chemical shifts of the acetylenic carbon atoms are influenced in two ways:
by charge transfer to the triple bond as in C CO, or from the triple bond as in magnified image
by polarisation of the charge in the triple bond in the above‐mentioned systems and in C  CS.
Conformation of open‐chain compounds. Part 3. Carbon‐halogen stretching frequencies and conformation of some vicinal dihalides
Authors: Altona C. , Hageman H.J. 
Published: September 2010

AbstractA study of the infrared and Raman spectra of some vicinal dihalogeno‐ethanes, ‐propanes and ‐butanes with predominant antiperiplanar orientation in the straight chain and branched series, reveals that the two C‐Hal stretching frequencies occur characteristically as a more or less strongly coupled pair: an intense Raman band (νs) and a strong infrared active mode of vibration (νas) at lower frequencey.The C‐Hal frequencies of the gauche conformations are weakly coupled.The position of the bands and the difference Δν = νs − νas are functions of the chemical/geometrical structure in the vicinity of the C‐Hal bonds. Empirical rules are presented by which the C‐Hal frequencies or, in strongly coupled systems, the average frequency of anti as well as of gauche forms can be predicted with fair accuracy.
The conformation of non‐aromatic ring compounds. Part 39. Dipole Moments and Conformational Properties of some trans‐1, 2‐Dihalogenocyclohexanes and their alkyl derivatives
Authors: Hageman H.J. , Havinga E. 
Published: September 2010

AbstractA number of trans‐1,2‐dihalogenocyclohexanes and their alkyl homologues have been synthesized and their dipole moments determined in carbon tetrachloride and in benzene. The diaxial conformation is found to be favoured except in cases of considerable syn‐diaxial crowding. From the dipole data of some 4‐methyl derivatives a “ΔG°e‐a” of 1.8 kcal/mole for the methylgroup has been calculated. Similar calulations have led to much lower ΔG°e‐a values in the case of 1‐alkyl derivatives: 0.6 kcal/mole for the methyl group and 1.1 kcal/mole for the ethyl group. Values of ∼ 3.5 kcal/mole have been calculated for the syn‐diaxial methyl ‐ bromine interaction in some 4,4‐dimethyl derivatives. Values of 2‐3 kcal/mole have been obtained for the corresponding methyl ‐ chlorine interaction.The magnitude of the aa ± ee equilibrium shift towards the ee form going from carbon tetrachloride to benzene as a solvent, seems to be characteristically constant (0.5 kcal/mole) in the case of the trans‐1,2‐dibromo(chloro)‐ cyclohexanes and ‐alkylcyclohexanes.
The heat of combustion of benzoic acid NBS standard sample 39i
Authors: Mosselman C. , Dekker H. 
Published: September 2010

AbstractThe heat of combustion of benzoic acid NBS standard sample 39i supplied by the National Bureau of Standards (Washington) was measured. The mean value under standard bomb conditions was found to be:26431.9 ± 1.6 J per gram.Measures leading to a high precision are given. Systematic errors were studied.
Ester hydrolysis in concentrated sulfuric acid
Authors: van Bekkum H. , Buurmans H. M. A. , Wepster B. M. , van Wijk A. M. 
Published: September 2010

AbstractAliphatic and alicyclic esters are found to be hydrolyzed conveniently and without epimerization in concentrated sulfuric acid at room temperature. First‐order kinetics are observed. A Hammett rho value of ‐3.6 applies for the hydrolysis of methyl benzoates. Sterically hindered esters show increased rates of hydrolysis. These findings are in accordance with the AAc 1 mechanism.
New musk odorants VI. The formation of 1,1‐dimethyl‐7‐isopropyltetralinviaa novel rearrangement‐dehydrogenation of longifolene
Authors: Kettenes D. K. , van Lierop J. B. H. , van der Wal B. , Sipma G. 
Published: September 2010

Abstract1,1‐Dimethyl‐7‐isopropyltetralin (II) is formed in up to 40% yield by a ZnCl2‐catalyzed rearrangement‐dehydrogenation of longifolene (I), or isolongifolene (III). The structural proof of II is based on spectroscopic and chemical evidence. Acetylation and formylation of II yielded products with a weak musk odour.
The synthesis of some bicycloheterenes
Authors: Wynberg Hans , Klunder A. J. H. 
Published: September 2010

AbstractThis paper deals with the synthesis of some bicycloheterenes. 4,5,6,7‐Tetrahydro‐1,3‐dimethyl‐4,7‐methanobenzo[c]thiophene (I), 4,5,6,7‐tetrahydro‐1, 3‐dimethyl‐4,7‐ethanobenzo[c]thiophene (II), 4,7‐dihydro‐1, 3‐dimethyl‐4,7‐ethanobenzo[c]thiophene (III) and 4,5,6,7‐tetrahydro‐1,3‐dimethyl‐2‐phenyl‐4,7‐ethanobenzo[c]pyrrole (IV) were obtained by ring‐closure of the corresponding bicyclic 1,2‐diacetyl compounds.
Poisoning effects of hydrogen sulfide on noble metal electrodes Part II. Effect of H2S on periodic current vs. potential curves of Pt and Au electrodes in 0.5 M H2SO4
Authors: Ijzermans A. B. 
Published: September 2010

AbstractPeriodic current vs. potential curves have been measured on Pt, platinized Pt, Au and Au/Pt electrodes in 0.5 M H2SO4 saturated with H2S, and a comparison has been made with curves obtained in H2S‐free solutions. It may be seen that the current peaks characteristic of the reactions of chemisorbed oxygen and hydrogen are suppressed for the greater part under the influence of H2S.
The ligand properties of pyridine‐N‐oxide. Extension and discussion
Authors: Reedijk J. 
Published: September 2010

AbstractA number of 15 new solvates containing pyridine‐N‐oxide of the general formula M(C5H5NO)mn+ (anion)n− is reported. In these compounds M = Li, Na, Mg, Ca, Sr, Ba, Mn, Fe, Co, Cu, Zn, Cd, Pb, and Tl, n = 1‐3, m = 3‐8, and the anions are ClO4− and BF4−.The compounds are identified by chemical analysis and by means of physical measurements.The shift towards lower wave numbers in the N‐O stretching frequency of the complexes is discussed. Far‐infrared spectra in the region 700‐200 cm−1 have also been investigated. A correlation between νNO and νMO is reported.Ligand‐field spectra for the transition‐metal solvates of Co(II) and Ni(II) have been re‐investigated. New values for Dq and B are reported, and the ligand is placed in the spectrochemical and nephelauxetic series.The Mössbauer spectrum of Fe(C5H5NO)6(ClO4)2 is discussed. Electron paramagnetic resonance spectra of the solvates of Mn(II), Ni(II), and Cu(II) have been investigated. No static Jahn‐Teller distortion of the species Cu(C5H5NO)62+ is observed at room temperature.Pyridine‐N‐oxide is concluded to be a rather strong ligand, as reflected by the facts that preparation of metal solvates is often possible from the hydrated metal salts without dehydration, and the rather high values of Dq/B calculated from the spectra of the cobalt(II) and nickel(II) solvates.
Reaction of α,β‐unsaturated ethers, amines, thioethers and selenoethers with lithium in liquid
Authors: Brandsma L. , Schuijl P. J. W. 
Published: September 2010

Abstractα,β‐Unsaturated thioethers RCH=CHSR′ (R=H, alkyl; R′ = alkyl, ‐CH=CHR, ‐C≡CR) and RC≡CSR′(R =alkyl;R′ = alkyl, ‐C≡CR) are cleaved by lithium in liquid ammonia to afford alkenethiolates RCH=CHSLi and alkynethiolates RC≡CSLi, respectively. Subsequent alkylation with R″Br gives the analogous α,β‐unsaturated thioethers RCH=CHSR″ and RC≡CSR″ in good to excellent yields. A similar result is obtained with the selenoether (CH3CH=CH)2Se.1‐Ethoxy‐1‐pentyne C3H7C≡COC2H5 and 1‐(N,N‐diethylamino)‐1‐hexyne C4H9C≡CN(C2H5)2 are reduced to trans‐C3H7CH=CHOC2H5 and trans‐C4H9CH=CHN(C2H5)2 with good yields. Treatment of ketene dithioacetals RCH=C(SR′)2 (R = H or alkyl, R′ = alkyl) with two equivalents of lithium and subsequent addition of ammonium chloride or water affords dithioesters magnified image.
The crystal structure of “anhydrous manganic acetate”
Authors: Hessel L. W. , Romers C. 
Published: September 2010

Abstract“Anhydrous manganic acetic” is a linear polymer with the empirical formula [Mn3O(OAc)6 · AcOH · OAc]n. The three manganese atoms in the monomeric unit are mutually connected by three pairs of acetate bridges and form an equilateral triangle with an oxygen atom in its centre. Acetic acid molecules and acetate bridges between the monomeric units complete the distorted octahedral coordination about the manganese atoms.
Base induced reactions of 1‐alkoxy‐ or l‐methylthio‐l‐(α‐ or β‐hydroxyalkyl)allenes. Formation of 3‐alkoxy‐ and 3‐methylthiodihydrofurans
Authors: Hoff S. , Brandsma L. , Arens J. F. 
Published: September 2010

Abstractl‐Alkoxy‐l‐(α‐hydroxyalkyl)allenes R1CH=C=C(OR2)C(OH)R3R4 (Ia) have been converted with high yields into 3‐alkoxy‐2,5‐dihydrofurans (II) using potassium tert‐butoxide in dimethyl sulfoxide. Hydrolysis of II with dilute sulfuric acid afforded 3‐oxotetrahydrofuran derivatives III. l‐(β‐Hydroxyalkyl)‐l‐methylthioallenes R1CH=C=C(SCH3)CH2CH2OH (IVb) and the analogous oxygen compounds IVa yielded 2‐alkyl‐3‐methylthio‐4,5‐dihydrofurans (Vb) and a mixture of 3‐methoxy‐2‐methyl‐4,5‐dihydrofurans (Va) and 3‐methoxy‐2‐methylenetetrahydrofuran VI, respectively. The preparation of the hydroxyallenes is described.
Potassium tert‐butoxide‐catalyzed isomerization of methyl linoleate in tert‐butanol and mixtures of tert‐butanol and ethylene glycol dimethyl ether: A kinetic investigation
Authors: Korver O. , Boelhouwer C. 
Published: September 2010

AbstractA kinetic investigation is reported of the potassium tert‐butoxide catalyzed isomerization of methyl linoleate in tert‐butanol and mixtures of tert‐butanol and ethylene glycol dimethyl ethers.The product is a mixture of 9cis, 11 trans and 10trans, 12cis methyl octadienoates.The reaction is first order in olefin and 1.5 order in base over the entire range of base concentrations (0.05 to 1 M).The order in base and the acceleration of the reaction by addition of ethylene glycol dimethyl ethers are discussed.