Abstract

A mixture of regioisomeric 2-bromo-1-indanyl and 1-bromo-2-indanyl 2-propynyl ethers was obtained in 10.5:1 ratio and separated by chromatography. Radical cyclization of the prevailing isomer in the presence of [chlorobis(dimethylglyoximato)(pyridine)]cobalt(III) (cobaloxime) afforded 3-methylenetetrahydrofuran fragment; the oxidation of the latter with excess chromium(VI) oxide complex with pyridine in dichloromethane furnished a new α-methylene-γ-butyrolactone in 59% yield.

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