Reactions of N-nitrenes with allyl aryl sulphides: N-heteroarylsulphenamides

Abstract

Oxidation of N-aminophthalimide, 3-aminobenzoxazol-2(3H)-one, and 1-amino-2-quinolone with lead tetraacetate in the presence of various substituted allyl aryl sulphides gives the corresponding N-allyl-N-heteroaryl-sulphenamides by [2,3] sigmatropic rearrangement of the intermediate N-heteroarylsulphimides. The n.m.r. spectra of thè sulphenamides sometimes show evidence for the presence of diastereoisomers, and a diastereoisomer has been isolated in pure form in one case. An explanation is offered for the widely differing thermal stabilities of these sulphenamides.