Aryne chemistry. Part XXXI. Reactions of arynes with αβ-unsaturated aldehydes
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2903-2910
- https://doi.org/10.1039/p19720002903
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.Keywords
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