Tetrahedron Letters

Synthesis of 2-cyano-1, 4-cycloheptadiene derivatives via divinylcyclopropane rearrangement and alkylation of novel cycloheptadienyl anion species

T Yamada, F Yoshimura, K Tanino

Index: Yamada, Takumasa; Yoshimura, Fumihiko; Tanino, Keiji Tetrahedron Letters, 2013 , vol. 54, # 6 p. 522 - 525

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Citation Number: 4

Abstract

An efficient synthetic method for 2-cyano-1, 4-cycloheptadiene derivatives was developed on the basis of divinylcyclopropane rearrangement. The substrates were prepared from 2- vinylcyclopropanecarbonitrile and an α, β-epoxysilane through a Peterson olefination. The resulting 2-cyano-1, 4-cycloheptadiene underwent deprotonation at the doubly allylic methylene group to afford a novel cycloheptadienyl anion, a useful intermediate for ...