A Comparison of the Reactivity and Mutagenicity of N-(Benzoyloxy)-N-(benzyloxy) benzamides

SA Glover, GP Hammond, AM Bonin

Index: Glover, Stephen A.; Hammond, Gerard P.; Bonin, Antonio M. Journal of Organic Chemistry, 1998 , vol. 63, # 26 p. 9684 - 9689

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Citation Number: 36

Abstract

A new series of N-(acyloxy)-N-alkoxybenzamides, N-(benzoyloxy)-N-(benzyloxy) benzamides 7 have been synthesized and have been found to be direct acting mutagens in Salmonella TA100. They undergo AAl1 solvolysis to give N-benzoyl-N-(benzyloxy) nitrenium ions 3 under conditions of acid catalysis as well as unusual BAl2 reactions at nitrogen with hydroxide. The latter process affords as intermediates the anomeric hydroxamic esters 4 ...