Abstract
Synthesis of alkenyl sulfides and their application to carbon-carbon bond forming reactions are described. Both (E) and (Z) -alkenyl sulfides were prepared stereoselectively by the following sequence of reactions : 1) the reaction of electrophiles with 1- (phenylthio) vinyllithium reagents prepared by the treatment of 2-methoxy-alkyl sulfides with twice molar amounts of BuLi. 2) photo-isomerization of alkenyl sulfides. 3) the coupling reaction of Grignard reagents with β- (phenylthio) -β, γ-unsaturated alcohols. New methods for carbon-carbon bond formation at both α and β to the phenylthio group of alkenyl sulfide via thionium ion or 2- (phenylthio) alkyltitanium intermediates were developed. Further alkenyl sulfides were found to be useful intermediates for the preparation of γ-oxoesters, furans, 1-cyclobutenyl ketones, and allenes. The related reactions such as the desulfurizative metallation of sulfides and the synthesis and reactions of cyclobutyl sulfides are also described.
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