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.
No takes yet. Share an insight, caveat, or question.
Heaney et al. (1972) studied this question.
Synapse has enriched 5 related papers. Consider them for comparative context: