Issue 0, 1972

Aryne chemistry. Part XXXI. Reactions of arynes with αβ-unsaturated aldehydes

Abstract

The reaction of benzyne, generated from anthranilic acid, benzothiadiazole 1,1-dioxide, and diphenyliodonium-2-carboxylate, with cinnamaldehyde results in the formation of flav-3-ene. Similarly tetrachlorobenzyne, generated from tetrachloroanthranilic acid, tetrachlorobenzenediazonium-2-carboxylate hydrochloride, and 3,4,5,6-tetra-chloro-2-(3,3-dimethyltriazeno)benzoic acid, affords 5,6,7,8-tetrachloroflav-3-ene. Reactions with other αβ-un-saturated aldehydes result in the formation of derivatives of 2H-chromen. The mechanism of the reaction has been studied using 14C, 2H, and alkyl groups as labels.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 2903-2910

Aryne chemistry. Part XXXI. Reactions of arynes with αβ-unsaturated aldehydes

H. Heaney, J. M. Jablonski and C. T. McCarty, J. Chem. Soc., Perkin Trans. 1, 1972, 2903 DOI: 10.1039/P19720002903

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