1,3-dipolar cycloaddition reactions of N-methyl-C-substituted-phenylnitrones with N-methylmaleimide


Agirbas H., Guner S.

HETEROCYCLIC COMMUNICATIONS, vol.6, pp.557-562, 2000 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 6 Issue: 6
  • Publication Date: 2000
  • Doi Number: 10.1515/hc.2000.6.6.557
  • Title of Journal : HETEROCYCLIC COMMUNICATIONS
  • Page Numbers: pp.557-562

Abstract

1,3-Dipolar cycloaddition reactions of N-methyl-C-substituted phenylnitrones with N-methylmaleimide were studied. The reaction of p-dimethylamino and 4-benzyloxy-3-methoxy substituted phenylnitrones with N-methyl maleimide gave only cis cycloadducts. Contrarily, the reaction of p-nitro and p-chloro substituted phenylnitrones with N-methylmaleimide gave cis and trans cycloadducts. The substituent effects on the stereochemistry of N-methyl-C-substituted phenylnitrone cycloaddition reactions are discussed.