Reactions of 2-(α-Haloalkyl) thiiranes with nucleophilic reagents: V. Reactions of 2-(α-Chloroalkyl) thiiranes with organolithium compounds

AA Tomashevskii, VV Sokolov, AA Potekhin

Index: Tomashevskii; Sokolov; Potekhin Russian Journal of Organic Chemistry, 2010 , vol. 46, # 12 p. 1822 - 1825

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Abstract

Abstract 2-(α-Haloalkyl) thiiranes reacted with methyl-, butyl-, and phenyllithium to give the corresponding allyl sulfides. The reactions of diastereoisomeric erythro-and threo-2-(1- chloroethyl) thiiranes with phenyllithium were stereospecific, and they afforded (E)-and (Z)-1- phenylsulfanylbut-2-enes, respectively. 3-Chloromethyl-2, 2-dimethylthiirane and phenyllithium gave rise to a mixture of 3-methyl-3-phenylsulfanylbut-1-ene and 3-methyl-1 ...