Sulphenyl azides

Sulphenamides.—A variety of bivalent sulphur compounds act as sulphenyl-ating reagents towards amines, giving sulphenamides, and most routes to these compounds are of this type. The copper(i)-catalysed reaction of azides with alkanethiols gives sulphenamides, in addition to the corre> sponding primary amine and disulphide arenethiols give only amine and disulphide, the sulphenamide being entirely converted into these products. 

Adducts (186) were formed by the regiospecific, but nonstereospecific, reaction of diphenylnitrilimine with diaryl sulphines." Sulphines of the type (187) reacted with aromatic sulphenyl chlopdes in a thiophilic manner, yielding (188). The sulphenic acid (189), a tautomer of (187), was considered as the reactive species in the latter reaction. The nucleophilic attack of azide ions on thiobenzoyl chloride S-oxide gave the yellow, very unstable sulphine (190), which decomposed rapidly to ben-zonitrile at room temperature with the evolution of gas, but which at -80 C could be characterized by means of i.r. spectroscopy. 9-Thiofluorenone... 

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