Sulphenamides and Selenenamides

Rotational barriers in arenesulphenamides, established by dynamic H n.m.r. spectroscopy, are considered to arise from a balance of steric and electronic 

Michida, Ghent. Pharnt. Bull., 1979,27,2093. 

Sulphenimines ArSN=CR C02R are formed from an arenesulphenyl chloride with an a-amino-acid ester in the presence of an acid scavenger, and they yield crketo-esters by reaction with PPhj and silica gel. Sulphenimines PhSN= CR CHjR are formed by the alkylation of carbanions formed from a thiolate and a nitrile.  

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