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Note | Regular issue | Vol 60, No. 7, 2003, pp.1673-1680
Published online, 23rd May, 2003
DOI: 10.3987/COM-03-9779
Thermal Rearrangement of Phenyl-substituted Ketene Ethylene Acetals

Mitsunori Oda,* Kazuo Morimoto, Nguyen Chung Thanh, Reina Ohta, and Shigeyasu Kuroda

*Department of Applied Chemistry, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan

Abstract

Thermal rearrangement of mono-, di-, and triphenyl-substituted ketene ethylene acetals was studied. Pyrolysis of all of these acetals provided phenyl-substituted tetrahydro-2-furanones as a major product. The more phenyl groups substitute on the ketene acetal skeleton, the lower reaction temperature was required for the rearrangement. In the cases of the diphenylketene acetals at high temperatures, fragmentation products, such as fluorene and benzophenone, probably derived from dipheylcarbene via diphenylketene, were observed.