Synthese und Dimroth‐Umlagerung von disubstituierten 5‐Imino‐1,2,4‐dithiazolidin‐3‐thionen (Senfölsulfiden)

Abstract

Synthesis and Dimroth Isomerization of Disubstituted 5‐Imino‐1,2,4‐dithiazolidine‐3‐thiones (Mustard Oil Sulfides).Treatment of N‐substituted dithiocarbamates with N‐substituted S‐chloroisothiocarbamoyl chlorides leads to disubstituted 5‐imino‐1,2,4‐dithiazolidine‐3‐thiones. Educts with different aromatic substituents give the diaryl derivatives 5, as expected by the reaction equation. Educts with one aromatic and one aliphatic substituent give 5‐alkylimino‐4‐aryl derivatives 10, regardless which starting component (3, 4, 7, 8) possesses the aliphatic or aromatic substituent. Educts with different aliphatic substituents (7, 8) leads to mixtures of isomeric derivatives 12, 13. Disubstituted 5‐imino‐1,2,4‐dithiazolidine‐3‐thiones with 5‐alkylimino group are able for Dimroth isomerization to 4‐substituted 2‐alkyl‐1,2,4‐thiadiazolidine‐3,5‐dithiones.