Arylation of Unsaturated Systems by Free Radicals. II. Arylation of Maleimide by Diazonium Salts1, 2

CS Rondestvedt Jr, O Vogl

Index: Rondestvedt; Vogl Journal of the American Chemical Society, 1955 , vol. 77, p. 2313

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Citation Number: 27

Abstract

Maleimide and N-substituted maleimides are arylated by diazonium salts in aqueous acetone at pH 3 in the presence of cupric chloride (Meerwein reaction). a-Arylmaleimides are formed in 20-55% yield. The yield is lowest with unsubstituted phenyl and it increases with the introduction of either electron-attracting or electron-releasing substituents into the para position. The arylmaleimides can be hydrolyzed readily and recyclized to arylmaleic ...