Insertion of sulfonylnitrenes into the carbon-hydrogen bonds of saturated hydrocarbons. Acid-catalyzed thermolysis of N-alkyl sulfonamides

DS Breslow, EI Edwards, EC Linsay…

文献索引：Breslow,D.S. et al. Journal of the American Chemical Society, 1976 , vol. 98, p. 4268 - 4275

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被引用次数: 31

摘要

Abstract: Alkanesulfonylnitrenes, generated by azide thermolysis, are relatively unselective reagents; methane-and 1-pentanesulfonylnitrenes insert into the primary, secondary, and tertiary CH bonds of 2, 4-dimethylpentane in the ratios 1: 2.3: 6.0. The insertion of methanesulfonylnitrene into the tertiary CH bonds of cis-and trans-1, 2-dimethyIcyclohexane is completely stereospecific, even under conditions which should favor intersystem ...