Abstract
Abstract The enolates, generated from phenacyl bromides by sodium telluride, yield 2,4-diarylfurans in addition to the expected dehalogenation products. No 1,4-dicarbonyl compounds could be isolated even in the presence of excess oxidizing agent, copper(II) chloride. Condensation of 2-(methoxymethoxy)arenecarbaldehydes with ethyl bromoacetate in the presence of sodium telluride gave the expected α,β-unsaturated esters which resisted cyclization to yield the desired coumarin derivatives. Attempted intramolecular Reformatsky-type reaction of 2-(bromoacetoxy)benzaldehyde gave only 6,12-epoxy-6H,12H-dibenzo[b,f]-[1,5]dioxocin as the major product.
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