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Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions

Fawcett, John and Griffith, Gerry A and Percy, Jonathan and Uneyama, Emi (2004) Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions. Organic Letters, 6 (8). pp. 1277-1280. ISSN 1523-7060

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Abstract

Topologically mobile difluorinated cyclooctenones undergo rapid, high-yielding, and completely stereoselective epoxidations with methyl-(trifluoromethyl)dioxirane. The epoxides resist conventional hydrolysis but react smoothly in basic media under microwave irradiation to afford unique hemiacetals and hemiaminals in good yield.