Ring-opening reactions of methylenecyclopropanes with diphenyl diselenide upon heating; formation of 3-phenylselenyl-2,5-dihydrofuran derivatives

Literature Information

Publication Date 2004-10-25
DOI 10.1039/B412823K
Impact Factor 6.222
Authors

Le-Ping Liu, Min Shi


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Abstract

The reactions of methylenecyclopropanes 1 with diphenyl diselenide give ring-opened products 2 in good yields at 150 °C under nitrogen atmosphere for 3 h; the products 2 can further undergo oxidative cyclization with hydrogen peroxide to furnish 3-phenylselenyl-2,5-dihydrofurans 3 in moderate yields (three steps) at room temperature in CH2Cl2 for 5 h; a plausible reaction mechanism has been proposed.

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