Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Effective Intramolecular Hydrogen Abstraction by the Sulfonamide Radical
Takehisa OhashiShinichi TakedaMitsuo OkaharaSaburo Komori
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1971 Volume 44 Issue 3 Pages 771-777

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Abstract

To study the reactivity of the sulfonamide radical in various reaction systems, the photodecomposition of N-t-butyl and N-methyl-N-chloroalkanesulfonamides was investigated. In benzene, the competitive hydrogen abstraction by the chlorine atom occurred to an appreciable extent and the participation of the chlorine atom was retarded with N2-flow control. In an aqueous solution (AcOH-H2O, t-BuOH-H2O), the quantitative conversion to γ-and δ-chloroalkanesulfonamide was observed; this was thought to be due to the intramolecular hydrogen abstraction by the sulfonamide radical and to the lowering of the reactivity of the chlorine atom because of the solvation by H2O. In an acid solution (AcOH-H2O-H2SO4), a higher preference for 1,5 hydrogen transfer was found; this was caused by the protonated sulfonamide radical. The formation ratio of γ- to δ-chloroalkanesulfonamide in several solvents was determined, and the reactivity of the sulfonamide radical was discussed. From the reaction products obtained, several aliphatic sultams were synthesized.

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