The sulphur(II)–nitrogen bond. Part III. The synthesis of the sulphur-(II)–nitrogen bond from sulphenates

Abstract

O-Methyl benzenesulphenate has been used to prepare a wide variety of sulphur(II)–nitrogen compounds. Sulphenamides are obtained in high yield from primary or secondary amines while the NN-dialkylsulphenamides can be prepared from NN-dialkylaminosilanes. With N-alkylaminosilanes, however, a mixture of N-alkyl and N-alkyl-N-trimethylsilylsulphenamides result, due to cleavage of Si–N and N–H bonds. N-Silylsulphenamides can be prepared from disilazanes, while N-methylbisbenzenesulphenimide MeN(SPh)₂ is obtained from N-methylbenzenesulphenamide.

Hydrazine oxidises O-methyl benzenesulphenate to diphenyldisulphide.