LDA-promoted decomposition of benzenesulfenamides. A route to aminyl radicals by dioxygen oxidation of lithium amides

A Barbieri, PC Montevecchi, D Nanni, ML Navacchia

Index: Barbieri, Anna; Montevecchi, Pier Carlo; Nanni, Daniele; Navacchia, Maria Luisa Tetrahedron, 1996 , vol. 52, # 41 p. 13255 - 13264

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Abstract

The LDA-promoted decomposition of N-monosubstituted sulfenamides 1a-d occurs through the formation of thioaminyl anions, which undergo oxidation either at sulfur, with formation of sulfonamides, or at nitrogen, with formation of thioaminyl radicals, depending on the nature of the 4′-substituent. The reaction of N, N-disubstituted sulfenamides 1e-h proceeds through the intermediacy of a lithium complex capable of generating aminyl radicals via ...