Tetrahedron

Dearomatization of furans via [2, 3]-Still–Wittig rearrangement

PA Caruana, AJ Frontier

Index: Caruana, Patrick A.; Frontier, Alison J. Tetrahedron, 2004 , vol. 60, # 48 p. 10921 - 10926

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Citation Number: 16

Abstract

Furans and benzofurans of type were dearomatized via the [2, 3]-Still–Wittig rearrangement. Enol ethers could be isolated or isomerized to the corresponding furans. The substitution pattern at the homofuranylic position had a strong influence on reaction behavior. Benzofurans rearranged with the greatest efficiency, and employment of a 3-substituted benzofuran (; R′= CH3) allowed the creation of a quaternary carbon center.