Sulphenamides and Related Compounds

Sulphenamides and Related Compounds.—Conventional synthetic routes to sulphenamides are represented with new systems in the recent literature. A sulphenyl chloride reacts with a hydrazone to give the sulphenamide ArCR= NNHSAr, and with an acid hydrazide to give the analogous product. Salts are formed between an arenesulphenyl chloride or a thiolsulphonate and a tertiary amine e.g. ArSCl + NEtg - ArSNEt, Cl ).  

Cyclization of an o-methoxycarbonylbenzenesulphenamide to a benziso-thiazolone is readily brought about by base.  

7V-Dialkylbenzeneselenenamides are generally similar to the corresponding sulphenamides in their selenenylation reactivity towards unsaturated systems.  

Dibenzenesulphenamide in benzene turns purple on oxidation with PbO, due to the formation of a stable (7 days) N-centred radical. An analogous radical is formed by homolysis of the N—N bond in a substituted arenesulphenyl-hydrazine.  

---