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Synthesis of a New α-Methylene-γ-butyrolactone Skeleton with the Use of Cobaloxime as Catalyst

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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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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Guilan University, P.O.Box 1914, Rasht, Iran

    K. Tabatabaian, M. Mamagkhani & T. Navai-Dyva

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  1. K. Tabatabaian
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  2. M. Mamagkhani
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  3. T. Navai-Dyva
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Tabatabaian, K., Mamagkhani, M. & Navai-Dyva, T. Synthesis of a New α-Methylene-γ-butyrolactone Skeleton with the Use of Cobaloxime as Catalyst. Russian Journal of Organic Chemistry 38, 210–212 (2002). https://doi.org/10.1023/A:1015509515669

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