Synthese und Reaktionen von Enaminosulfoniumsalzen / Syntheses and Reactions of Enaminosulfonium Salts

Abstract

A general method for preparing (E)-alkylamino and dialkylamino vinylsulfonium salts is reported. The hydrolysis and some alkylation and acylation reactions have been examined. The 2,2-dihydroxyethyl sulfonium salt (9 a) is produced by acid hydrolysis of 4 a. In the reaction of 4h with trimethyloxonium salt and acyl halides the N-alkylated and N-acylated products 4 a and 11 are formed respectively. (E)-N,N-diacylated compounds (12) are obtained from 41 and 51 by the reaction with excess acyl halides. On treatment with base, 11a forms mixtures of the (E)- and (Z)-sulfonium imido ylides 14 and 15.