Regioselectivity of the photochemical addition of ammonia, phosphine, and silane to olefinic and acetylenic nitriles

…, CM Breneman, JC Joseph, JP Ferris

Index: Guillemin, Jean-Claude; Breneman, Curt M.; Joseph, Jeffrey C.; Ferris, James P. Chemistry - A European Journal, 1998 , vol. 4, # 6 p. 1074 - 1082

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Citation Number: 29

Abstract

Abstract In most cases, the photochemical addition of NH 3, PH 3, and SiH 4 to olefinic and acetylenic nitriles proceeds by a radical chain pathway to give β-addition products (below). With NH 3 and olefinic nitriles, the organic radical formed is not sufficiently energetic to abstract a hydrogen atom from NH 3 and the reaction leads to α-adducts.