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 = ¿[anion radical][sulfonamide]. In the reaction of sodium naphthalenide (and probably sodium biphenylide) with the toluenesulfonamide of p-toluidine, electron transfer and cleavage are considerably faster than acid-base reaction with the acidic proton. Sodium anthracenide, however, reacts only as a base with this substrate. Gross structural effects on the scope of the reaction are discussed. The discovery of the efficient cleavage of arenesul-fonamides1 2 and toluenesulfonate esters3 with the anion radicals derived from aromatic hydrocarbons by treatment with alkali metals in ether solvents has prompted us to examine the mechanisms of these potentially useful reactions. Some results and conclusions concerning the anion radical cleavage of sulfonamides are presented in this paper.Preliminary examination of the reaction of several sulfonamides with sodium naphthalenide at room temperature in 1,2-dimethoxyethane (DME) indicated a rather variable stoichiometry. One equivalent of sul-(1) (a)

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Bei der Spaltung von Sulfonamiden sek. Amine, z.B. (I), mit Salzen von Aren‐Anionenradikalen, z.B. (II), erfolgt schnelle Reaktion zu Amid‐ und Sulfinat‐Anionen.