bluuebunny/crossref_metadata_2025_split huggingface dataset:
An SN(ANRORC) mechanism in the amination of phenyl‐1,3,5‐triazine with potassium amide in liquid ammo a A novel mechanism for the Chichibabin reaction
Authors: Simig Gy. , van der Plas H. C. 
Published: September 2010

AbstractThe amination of phenyl‐ 1,3,5‐triazine with potassium [15N]amide in [15N]ammonia has been investigated at −33°. It was observed that (i) a Chichibabin amination occurs at a very low rate, (ii) the amination occurs partly according to an SN(ANRORC) mechanism, (iii) a considerable amount of 15N is present in recovered starting material. All these results are explained by a series of equilibria between substrate ⇄ σ‐adducts ⇆ open‐chain amidines ⇄ product.
The discharge‐induced and the thermal reaction between methane and mixtures of bromine and chlorine
Authors: van Drumpt J.D. 
Published: September 2010

AbstractAs in the previously reported low‐ and high‐temperature photochemical reactions, preferred formation of CH3Br is observed when a gas mixture of the title reactants is exposed to the action of a “cold” electrical discharge (35°C) or to high temperatures (100‐450°C). The influence of the main reaction variables on product composition is discussed. It is suggested that the mechanism of CH3Br‐formation in the discharge reaction is largely analogous to that operative in the thermal and the photochemical processes. A crucial step in these reactions is the primary attack of a chlorine atom on methane. The different continous‐flow processes have approximately been optimized with respect to their CH3Br yield per pass (discharge reaction: 16%; thermal reaction: 62%). In addition, optimum energy yields with respect to CH3Br formation are compared. Of the four methods tested the high‐temperature photochemical reaction displays the most favorable combination of CH3Br yield and energy yield. The discharge method generally combines a high selectivity and energy yield with low conversions per pass, and may be attractive if recycling of reactants is possible.
Conversion of (‐)‐dihydrocodeinone into (‐)‐1‐methyldihydrocodeinone, (‐)‐1‐methyldihydrocodeine and (‐)‐1‐methyldihydrothebainone. (Chemistry of opium alkaloids, Part V)
Authors: Olieman C. , Maat L. , Beyerman H.C. 
Published: September 2010

AbstractChloromethylation of (‐)‐dihydrocodeinone (1) followed by reduction with zinc yielded, via 2, (‐)‐1‐methyldihydrocodeinone (3). Further reduction afforded (‐)‐1‐methyldihydrothebainone (4). The latter compound proved to be identical with (‐)‐1‐methyldihydrothebainone prepared by total synthesis. This proves position 1 of the chloromethylation and, in consequence, of the methyl group.Compound 3 could also be reduced catalytically to (‐)‐1‐methyldihydrocodeine (5).
Derivatives of cis‐NPCl2(NSOCl)2 and (NPCl2)2NSOCl Part III. Butylamino derivatives of cis‐NPCl2(NSOCl)2
Authors: van Den Berg J.B. , Klei E. , de Ruiter B. , van De Grampel J.C. , Kruk C. 
Published: September 2010

AbstractReaction of cis‐NPCl2(NSOCl)2 with n‐butylamine (molar ratio 1:2) in acetonitrile leads to a mono(amino) derivative, NPCl(NHBu) (NSOCl)2. Under the same experimental conditions sec‐butylamine gives a mixture of about equal amounts of NPCl(NH‐s‐Bu) (NSOCl)2 and NPCl2NSOClNSO(NH‐s‐Bu), while tert‐butylamine yields mainly NPCl2NSOClNSO(NH‐t‐Bu). The increasing tendency towards substitution at a sulfur atom can be ascribed to an increasing steric hindrance towards the formation of an 5N1 transition state with five coordinated phosphorus. The reaction of NPCl(NHBu) (NSOCl)2 with n‐butylamine (molar ratio 1:2) gives a geminal bis(n‐butylamino) derivative, which on fluorination yields NP(NHBu)2(NSOF)2. The 31P‐ and 19F NMR spectra of the compounds prepared are discussed.
A practical technique for laboratory Birch reductions (Chemistry of opium alkaloids, Part VI)
Authors: Beyerman H.C. , van Leeuwen F.F. , Lie T.S. , Maat L. , Olieman C. 
Published: September 2010

AbstractA practical technique and a simple apparatus are described, which makes possible various ways of carrying out Birch reductions on a (0.1−10 g)‐scale. Examples of reductions of 1‐benzylisoquinolines and β‐nitrostyrenes are discussed. Reaction of 1,2,3,4,5,8‐hexahydro‐1‐(3,5‐dihydroxy‐4‐methoxybenzyl)‐6‐methoxyisoquinoline (2b) with acetone yielded a hexahydrodimethylprotoberberine (3).
Réactions d'insertion 1−2,1−3 et 1−4 dans la liaison germanium‐phosphore de germaphospholannes
Authors: Couret C. , Escudié J. , Satgé J. , Redoulès G. 
Published: September 2010

AbstractThe 1−2 addition reactions of aldehydes on the germanium‐phosphorus bond of germaphospholanes lead to diastereoisomeric germoxyphosphepanes. An asymetric induction of the chiral phosphorus atom is observed with preferential formation of sterically favoured diastereoisomers. This stereochemistry seems to derive from a four‐centered insertion concerted mechanism. In the regio‐selective additions of conjugated ethylenic derivatives (acrylonitrile and methyl acrylate) the preferential formation of diastereoisomers is also observed. Phenylacetylene undergoes a radical insertion reaction into the intracyclic germanium‐phosphorus bond with formation of two ethylenic isomers. The reactions of germaphospholanes with cyclic ethers and α‐ethylenic aldehydes and ketones respectively lead, after 1−3 or 1−4 additions, to new germylated and phosphorylated 8 or 9 membered heterocycles. Oxidation and sulfuration reactions of germaphospholanes are also described.
Base‐induced deprotonation and ring opening of thiophene and some of its derivatives
Authors: Gräfing R. , Brandsma L. 
Published: September 2010

AbstractThiophene and its derivatives with R = H, alkyl or −SCH3 group in the 2‐ and 5‐positions (1 and 4) undergo the following types of reaction with strong bases, depending upon the nature of the base and the solvent or solvent mixture: if R = H or alkyl: abstraction of the 2‐ and 5‐proton in relatively apolar media and ring opening to enynethiolates in strongly polar media (HMPT); if R = CH3S: substitution on S in the SCH3 group by butyllithium in THF/HMPT, abstraction of a CH3S proton by butyllithium in THF (without HMPT) and ring opening in strongly polar media with LiN(i‐Pr)2.
The chemistry of small ring compounds. Part 35. Oxidation of arylcyclopropanone methyl hemiacetals by cupric ions and by oxygen
Authors: Bakker B.H. , Steinberg H. , de Boer Th. J. 
Published: September 2010

AbstractPhenylcyclopropanone methyl hemiacetals 1a−c can be smoothly oxidised by a variety of oxidising agents, the nature of which exerts a strong influence on the product distribution. The common key‐intermediate in all these reactions is the ring‐opened phenyl stabilised β‐propionate radical 3 (Schemes 1 and 3). When the oxidation is carried out with cupric nitrate in pyridine the main product is meso‐ and racemic dimethyl 3,4‐diphenyladipate 4.With cupric or ferric chloride in acetonitrile or methanol, the intermediate radicals 3a−c combine with a halogen atom in a ligand transfer reaction and afford methyl 3‐chloro‐3‐phenylpropionates 10a−c. Phenylcyclopropanone methyl hemiacetal la rapidly absorbs oxygen in the presence of a catalytic amount of cupric‐pyridine complex, giving methyl benzoylacetate 15 as the main product. Without this catalyst the absorption of one equivalent of oxygen is very sluggish and affords the methyl 3‐hydroperoxy‐3‐arylpropionate 13a. The hydroperoxide formation is notably slower in benzene than in CCl4 or CHCl3. In these chlorinated solvents, 2‐methyl‐2‐phenylcyclopropanone methyl hemiacetal 1c gives the peroxylactone 5‐methyl‐5‐phenyl‐1,2‐dioxolan‐3‐one 14.
Ring transformations in reactions of heterocyclic compounds with nucleophiles (XV) Reactions of N‐aminopyrimidinium salts with liquid ammonia
Authors: Roeterdink F. , van der Plas H.C. 
Published: September 2010

AbstractN‐Aminopyrimidinium salts, e.g. 4,6‐dimethylpyrimidinium (2a), 4,6‐diphenylpyrimidinium (2b) and 2,4,6‐trimethylpyrimidinium mesitylenesulfonates (2c), show a very divergent behaviour towards liquid ammonia at − 33°. 1) Proton abstraction takes place from the amino group of 2a, resulting in the formation of a 1,3‐dipolar intermediate, which under the reaction conditions dimerises. 2) Adduct formation is observed on C(2) of 2a or C(6) of 2c, resulting in the formation of a pyrazole or a 1,2,4‐triazole ring. 3) Deamination occurs with 2b and 2c, via two pathways, namely, a nucleophilic attack of ammonia on the nitrogen atom of the amino group or by a ring opening/ring closure sequence. This last‐mentioned mechanism has been proved by use of 15N‐labelled ammonia.
Electronic and e.s.r. spectra of compounds containing the tetrakisdithiocarbamato‐molybdenum(V) or ‐tungsten(V) cations
Authors: Nieuwpoort A. , Steggerda J.J. 
Published: September 2010

AbstractElectronic spectra and e.s.r. spectra of the compounds [M(R2dtc)4]X (M = Mo, W; R2dtc = R2NCS2−; R = Me, Et, i‐Pr, Ph, Bz; R2 = Tm, Pm, MeBz; Tm = (CH2)4; Pm = (CH2)5; X = halide) have been investigated. In the electronic spectra d‐d transitions, electron‐transfer bands, and internal ligand absorptions could be assigned. The d‐d transitions are fitted into the Ligand‐Field model, yielding for Mo(V): Dq = 2.95 kK, Cp = 0 kK, and λ = 460 cm−1, and for W(V): Dq = 3.38 kK, Cp = 0 kK, and λ = 1610 cm−1. The e.s.r. spectra show a very small g anisotropy. This cannot be fitted into the Ligand Field model, due to spin‐orbit coupling on the coordinated sulfur atoms. An Extended Hückel MO calculation for the molybdenum complex shows that 86% of the unpaired electron is in the metal xy orbital. The experimental g values show fair agreement with the results of the MO calculations.
Vinyl copper(I) compounds Part I: Stereospecific addition of heterocuprates to 1‐alkynes in tetrahydrofuran
Authors: Westmijze H. , Meijer J. , Bos H.J.T. , Vermeer P. 
Published: September 2010

AbstractIn this paper a study on the reactivity of various heterocuprates [RCuY]MgX 1 towards 1‐alkynes R′−C≡CH 2 in tetrahydrofuran is presented. In most cases a smooth cis addition was observed in this solvent generally leading, after protic work‐up, to terminal alkenes RR′CCH2 4a or sometimes to mixtures of alkenes 4a and non‐terminal E‐alkenes R′CHCHR 4b in excellent yields. Except for the reaction of [t‐BuCuBr]MgCl with Ph−C≡C−H no evidence was obtained of proton abstraction from the terminal alkynes 2 by the cuprates.The influence of CuBr and LiBr on the course of the addition reaction was studied in some cases.
Cyclohexaamylose modified with an oxime group: An enzyme model
Authors: van Hooidonk C. , de Korte D. C. , Meereboer M. A. C. Reuland 
Published: September 2010

AbstractA three‐step synthesis was utilized to introduce the nucleophilic oxime group, 2(hydroxyimino)ethyl, into cyclohexaamylose (CHA) at the 2‐O or 3‐O position. The rates of deacylation of p‐nitrophenyl acetate (PNPA) in aqueous solutions were determined without and in the presence of varying concentrations of O‐[2‐(hydroxyimino)ethyl]‐CHA (CHA‐Ox). From the observed Michaelis‐Menten‐like kinetics, the pH dependence and competitive inhibition experiments with cyclohexanol it was concluded that the deacylation is consistent with a reaction scheme involving a 1: 1 inclusion complex followed by a rate‐determining nucleophilic displacement of the p‐nitrophenoxide ion by the ionized oxime group.The CHA‐Ox cavity provides an effective binding site for PNPA resulting in a favourable orientation of the acyl residue with respect to the oxime group. The rate accelerations can be ascribed to an apparent increase in the local concentration of the reactive species. CHA‐Ox displays substrate specificity illustrated by using m‐nitrophenyl acetate and p‐nitrophenyl dimethylphosphinate as substrates.The CHA‐Ox/ester system represents a model for the acylation of hydrolytic enzymes.
The chemistry of small ring compounds. Part 36 CIDNP effects during the oxidation of substituted cyclopropanone methyl hemiacetals by di‐tert‐butyl diperoxyoxalate
Authors: Bakker B. H. , Bok Th. Reints , Steinberg H. , de Boer Th. J. 
Published: September 2010

AbstractThe reaction of tetramethylcyclopropanone methyl hemiacetal (2) and phenylcyclopropanone methyl hemiacetal (7) with di‐tert‐butyl diperoxyoxalate (TBPO) has been studied in connection with observed CIDNP effects. Oxidation of these hemiacetals by tert‐butoxyl radicals (generated from TBPO) gives rise to the ring‐opened radical Me2 •CCMe2COOMe (3) and C6H5•CHCH2COOMe (8) respectively. The existence of radical 3 is clearly demonstrated in benzene solution by the observed A/E multiplet effect for the disproportionation products HCMe2CMe2COOMe and H2CCMeCMe2COOMe, formed from two radicals 3 in a radical pair. In CDCl3 solution, however, emissions are found for the unsaturated ester, CHCl3 and CHDCl2, and an A/E signal for the saturated ester. The chlorinated products are formed from the •CCl3 and •CDCl2 radicals and a hydrogen donor.The benzylic radical 8 gives rise to an A/E multiplet effect (in benzene) for the combination product dimethyl 3,4‐diphenyladipate (9) and the disproportionation product methyl cinnamate (11).
Folded conformations. Part VIII. Does intramolecular donor/acceptor interaction affect the basicity of p‐(N,N‐dimethylamino)benzyl p‐nitrophenyl sulfone?
Authors: Bleeker I. P. , Engberts Jan B. F. N. 
Published: September 2010

AbstractComparison of the equilibrium basicity of the title sulfone (1) with that of some reference compounds indicates that the ground state of 1 is not affected by intramolecular charge transfer from the donor to the acceptor ring.
Chemistry of tetraalkoxyethenes VIII Hydrolysis and subsequent decarboxylation of ethyl 2,2,3,3‐tetraalkoxy‐1‐cyanocyclobutanecarboxylates
Authors: Ooms P. H. J. , Bos R. P. , Scheeren J. W. , Nivard R. J. F. 
Published: September 2010

AbstractTreatment of ethyl 2,2,3,3‐tetraalkoxy‐1‐cyanocyclobutanecarboxylates (7), obtained by heating tetraalkoxyethenes with ethyl 2‐cyano‐2‐alkenoates at 100°, with a dilute methanolic solution of sodium hydroxide at 50° leads to hydrolysis of the ester function. On prolonged heating at higher temperatures the resulting products 8 decarboxylate, yielding 2,2,3>3‐tetraalkoxycyclobutanecarbonitriles 9. Under these conditions the nitrile group is also partly hydrolysed to a carboxylic acid function. Depending on the pH, acidification of 8 yields either rearranged, six‐membered ring compounds, viz. 4,4,5,5‐tetraalkoxy‐2‐cyano‐δ‐valerolactones 12, or acyclic acetals of α‐keto esters 13.
A reinvestigation of the mechanism of the amination of 5‐bromo‐4‐t‐butylpyrimidine. On the occurrence of an SN(ANRORC) mechanism
Authors: Rasmussen C. A. H. , van der Plas H. C. 
Published: September 2010

AbstractEvidence is presented that the cine‐substitution of 5‐bromo‐4‐t‐butyl[1(3)‐15N]pyrimidine into 6‐amino‐4‐t‐butyl[x‐15N]pyrimidine by potassium amide in liquid ammonia takes place to a considerable extent via an 5N(ANRORC) mechanism involving an addition of amide ion to C(2) of the pyrimidine ring. The currently accepted view that this conversion proceeds via a “hetaryne mechanism” has to be revised.
The photochemistry of previtamin D and tachysterol
Authors: Jacobs H. J. C. , Boomsma F. , Havinga E. , van der Gen A. 
Published: September 2010

AbstractPathways of formation are discussed for the thirteen toxisterols, the isolation and structure determination of which have been dealt with in the preceding article. It is suggested that toxisterols A (C‐8 spiro compounds) and C (bicyclo[3.1.0]hexenes) originate from previtamin D through relaxation of the excited“tZc”form of its hexatriene system. The symmetry‐allowed conrotatory closure to a 5–6–10 cyclopropane ring constitutes a plausible first step for both reactions. The description of the formation of the bicyclohexene moiety of toxisterol C1 as a two‐step process is consistent with its stereochemistry; the configuration corresponds to an overall [π4a+π2a] route and not to the [π4s+π2a] pathway expected for a concerted photochemical process. For the formation of toxisterols A a series of steps following the initial cyclopropane ring closure ‐ comprising a hydrogen shift from C‐4 to C‐9 and bond formation between C‐4 and C‐8 ‐ to provide the C‐8 spirostructure is proposed. Toxisterol D1 can be formed from previtamin D (or tachysterol) by a photoinduced antarafacial [1,5] hydrogen shift. The cyclobuteno compound toxisterol E1 originates from excited tachysterol through a disrotatorye ring closure of the 6‐7‐8‐9 butadiene moiety.A rationalization is offered for the novel photochemical 1,6‐addition of alcohol to the conjugated triene system of previtamin D/tachysterol yielding the toxisterols B, as well as for the photoreduction to form toxisterol R1. The article concludes with comments on the general picture of photoconversions as it emerges from previous and present investigations.
Redox properties of copper, nickel and palladium complexes with amidato ligands
Authors: Bour J. J. , de Brugh‐Arts J. H. M. Aan , Hendriks H. M. J. , Steggerda J. J. 
Published: September 2010

AbstractCu(II), Ni(II) and Pd(II) complexes of the terdentate ligands 1‐(2‐pyridylmethylene)biuret and 1‐(2‐hydroxylphenyl)biuret (abrv. as pybiH2 and phHbiH2, respectively) have been prepared and their spectral, magnetic and voltammetric properties studied. In a square‐planar coordination the metals are bonded to the pyridine N (in the pybi compounds) or to the phenolato O (in the phHbiH2 compounds) and to one or two deprotonated amide N's in [Cu(pybiH)(H2O)]+, Pd(pybiH)Cl and [Cu(phbiH)]2 respectively in Cu(pybi)(H2O) and [Ni(pybi)(OH)]− Comparison with other biuretato complexes of Cu reveals that increasing the number of coordinated amide N's goes parallel with increasing energy of the spectral dd transition and with a decrease of half wave potentials for the oxidation to Cu(III) as well as for the reduction to Cu(I) compounds. The redox orbitals seems to be located mainly on the metal centre in accord with previous MO calculations.
The electrocatalytic reduction of nitrogen compounds Part I: The electrochemical reduction of nitrite at a rotating platinum ring‐disc electrode
Authors: van der Plas J. F. , Barendrecht E. 
Published: September 2010

AbstractThe mechanism of the electrochemical reduction of nitrite has been studied at a rotating ring‐disc electrode. It is found that the reduction of nitrite to nitric oxide is a reversible process. The reduction of nitric oxide to hydroxylamine involves the intermediate HNO, from which dinitrogen oxide can be formed in a side reaction to the reduction process.
Beckmann rearrangement of aldoximes catalyzed by transition metal salts: Mechanistic aspects
Authors: Leusink A. J. , Meerbeek T. G. , Noltes J. G. 
Published: September 2010

AbstractThe Beckmann rearrangement of aldoximes catalyzed by transition metal salts proceeds by a dehydration‐hydration reaction. A mechanism is proposed in which nitrile is bound to an oxime‐metal complex; subsequently, water (as OH− and H +) is transferred from oxime to nitrile in the ligand sphere of the metal, yielding nitrile and amide, respectively.
Derivatives of meta‐di‐tert‐butylbenzene. Part IV Dissociation constants of 2‐halogeno‐3,5‐di‐tert‐butylbenzoic acids
Authors: de Koning Adrianus Jan 
Published: September 2010

AbstractThe preparation of 2‐chloro‐, 2‐bromo‐ and 2‐iodo‐3,5‐di‐tert‐butylbenzoic acid is described and a possible explanation for their unexpectedly high dissociation constants is given.
The photo‐oxidation of hexamethylbenzene by singlet oxygen
Authors: van den Heuvel C.J.M. , Steinberg H. , de Boer Th.J. 
Published: September 2010

AbstractIn the dye‐sensitized photo‐oxidation of hexamethylbenzene two molecules of singlet oxygen are rapidly taken up: one of the oxygenation steps involved is an ene‐type reaction, and the other a [4 + 2]‐cycloaddition. The resulting endoperoxy hydroperoxide 2 can be reduced selectively to the corresponding endoperoxy alcohol 3 and by further reduction to the triol 4. X‐ray analysis shows the hydroperoxy group and the OO bridge in 2 to be on different sides of the cyclohexyl ring.
Réarrangement de dérivés des thiolannones‐2
Authors: Brisset G. , Morin L. , Paquer D. , Rioult P. 
Published: September 2010

AbstractVarious nucleophiles (sodium methoxide, hydride ion, thiolates and carbanions derived from organomagnesium compounds and ketones) react with 3‐[bis(methylthio)methylene]‐2‐thiolanones giving a rearrangement. The mechanism of the proposed rearrangement has been investigated. The reaction of enolate ions with thiolanones produces new β‐diketones.
Total synthesis of methyl t‐5,c‐8,c‐11,c‐14‐ and c‐5,c‐8,c‐11,t‐14‐eicosatetraenoate and of t‐2,c‐5,c‐8,c‐11,c‐14‐eicosapentaenoic acid
Authors: Egmond G.J.N. , Pabon H.J.J. , van Dorp D.A. 
Published: September 2010

AbstractOn the basis of trans‐2‐hexene‐1,6‐diol and trans‐2‐octenol, both obtained by trans reduction of their acetylenic precursors with sodium in liquid ammonia, trans‐5‐eicosene‐8,1 1,14‐triynoic acid and trans‐ 14‐eicosene‐5,8,11‐triynoic acid were built up by classical methods. Partial hydrogenation and esterification afforded the desired eicosatetraenoates. In addition, reduction of previously described trans‐2‐eicosene‐5,8,11,14‐tetraynoic acid gave t‐2,c‐5,c‐8,c‐11,c‐14‐eicosapentaenoic acid.
Vapour phase chemistry of arenes. Part VII: Direct, thermal cyanation of benzene derivatives and pyridine by hydrogen cyanide
Authors: van Nierop Kees , Louw Robert 
Published: September 2010

AbstractBenzene, chlorobenzene or benzonitrile, in the presence of a little C2Cl6 or formaldehyde, reacts with HCN at ∼ 480° (30 s) to give the (mono)cyano derivatives. Features, especially isomer distributions for this cyanation closely resemble those for gas‐phase chlorination. By analogy, therefore, a free radical mechanism is advanced involving endothermal hydrogen abstraction by Cl• and/or H• to give aryl radicals, which in turn attack HCN at carbon, displacing hydrogen. Pyridine leads to cyanopyridines (89 % 2‐, 6 % 3‐, 5 % 4‐isomer), the 2‐position being ∼ 3 times as reactive as benzene hydrogens. This supports our view that differences in CH bond strength play a major part, as it is known that 2‐pyridyl is stabilized relative to its 3‐ and 4‐analogues. ICN was found not to be a suitable alternative for HCN.
Bis‐heterocycles. Part III.: Synthesis of tetramethylene‐3,3′‐di‐1,2,4‐triazoles and tetramethylene‐2,2′‐di‐1,3,4‐thiadiazoles
Authors: Ram Vishnu Ji , Pandey H.N. 
Published: September 2010

AbstractTetramethylene‐4,4′‐bis(1‐arylthiosemicarbazides) were converted into tetramethylene‐3,3′‐bis(4‐aryl‐5‐mercapto‐1,2,4‐triazoles) and tetramethylene‐2,2′‐bis[5‐(arylamino)‐1,3,4‐thiadiazoles] under different reaction conditions. The bis(5‐mercapto‐1,2,4‐triazoles) were converted into their thiolates on treatment with alkyl halides. Some compounds were found to be active pesticides.
Synthesis and chiroptical properties of (‐)‐(S)‐2‐chloro‐3‐(5‐imidazolyl)propanol (Imidazole chemistry, Part II)
Authors: Beyerman H.C. , van Weelderen A. W. Buijen , Maat L. , Noordam A. 
Published: September 2010

Abstract(‐)‐(S)‐2‐Chloro‐3‐(5‐imidazolyl)propanol (4) was synthesized by reduction of both the acid chloride and the methyl ester of (‐)‐(S)‐2‐chloro‐3‐(5‐imidazolyl)propionic acid. The optical rotatory dispersion and circular dichroism spectra are discussed.