An abnormal hydrolytic CN cleavage of the amide group in N-substituted 4-carbamoyltetradecachlorotriphenylmethyl radicals, and related reactions

…, J Riera, J Castañer, C Onrubia, JJ Ubierna

Index: Ballester, M.; Riera, J.; Castaner, J.; Onrubia, C.; Ubierna, J. J. Tetrahedron Letters, 1983 , vol. 24, # 20 p. 2121 - 2124

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Abstract

Summary: The alkaline hydrolysis of amides p (RCH, NHCO)-C6C14-~(C6C15) 2 (R, C02Et or C02H) occurs via methylene-nitrogen bond cleavage. Under the given conditions, the amide group in the corresponding non-radical, triarylmethane species, and in 4- (benzylcarbamoyl) tetradecachlorotriphenylmethyl radical, does not undergo any hydrolysis. That abnormal cleavage is traced therefore to the radical character.