Selective removal of electron-accepting p-toluene-and naphthalenesulfonyl protecting groups for amino function via photoinduced donor acceptor ion pairs with …

T Hamada, A Nishida, O Yonemitsu

Index: Hamada, Tatsuo; Nishida, Atsushi; Yonemitsu, Osamu Journal of the American Chemical Society, 1986 , vol. 108, # 1 p. 140 - 145

Full Text: HTML

Citation Number: 115

Abstract

Abstract: When N-tosylamines (3a, 3b, 7, 17a, 17b, 21, 23) in aqueous ethanol were irradiated with a high-pressure mercury lamp in the presence of an electron-donating aromatic such as 1, 2-(6) and 1, 4-dimethoxybenzenes (10) and 1, 5-dimethoxynaphthalene (14) and a reductant (sodium borohydride, ascorbic acid, ammonia borane, hydrazine), a photochemical detosylation proceeded quite easily to give the corresponding amines (4a, ...