Mechanism of sulfonamide cleavage by arene anion radicals

WD Closson, S Ji, S Schulenberg

Index: Closson; Ji; Schulenberg Journal of the American Chemical Society, 1970 , vol. 92, # 3 p. 650 - 657

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Citation Number: 66

Abstract

Abstract: In the cleavage of sulfonamides of secondary amines with arene anion radicals 2 moles of the reducing species are consumed rapidly, resulting in formation of amide and sulfinate anions. In the case of arenesulfinate ion a subsequent, much slower reduction converts this to arene hydrocarbon and a mixture of thiosulfate, sulfite, and sulfide salts. By analysis of competitive reactions, the rate law for the first step has been deduced as rate= ...