The sulphur(II)–nitrogen bond. Part I. Reaction of alkanesulphenyl chlorides with secondary amines

Abstract

The preparation of sulphenamides from alkanesulphenyl chlorides and amines is reported. gem-Diamines are formed by a side reaction, along with dialkyl disulphides and trisulphides. Thioformaldehyde is thought to be an intermediate, formed by what is probably a 1,2-elimination of hydrogen chloride from the sulphenyl chloride. Lithium methoxide gives dimethoxymethane, but no sulphenic ester, with methanesulphenyl chloride.