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 = k[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.
All Science Journal Classification (ASJC) codes
- Colloid and Surface Chemistry