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Reaction of Dimethylphenacylsulfonium Bromide with N -Nitrosoacetarylamides and Reactions of the Products with Nucleophiles

1976; Oxford University Press; Volume: 49; Issue: 1 Linguagem: Inglês

10.1246/bcsj.49.321

1348-0634

Ahmad Sami Shawali, Abdou O. Abdelhamid,

Cyclopropane Reaction Mechanisms

Abstract The azo coupling of dimethylphenacylsulfonium bromides (I) with N-nitrosoacetanilides in nonaqueous solvents, and with diazotized aniline in aqueous media gave 2-bromophenylglyoxal 2-arylhydrazones (V) and the tetrazine (VI), respectively. V reacted with nucleophiles displacing the bromide. Treatment of V with bases gave VI via benzoylphenylnitrilimine (X). 1,3-Dipolar cycloadditions of X onto ethyl acrylate and acrylonitrile afforded the expected cycloadducts. The mechanisms of the reactions are outlined.