Reaction of thiiranes with azomethine compounds

Thiiranes add to imines and oximes to give thiazolidines. The addition of asymmetrical thiiranes is regioselective. The reaction of derivatives of asymmetrical carbonyl compounds with methylthiirane leads to mixtures of cis and trans stereoisomers of thiazolidines. In the N-arylideneethylamine series the reaction is accelerated by donor substituents and is retarded by acceptor substituents.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 627–633, May, 1982.