Generation and stereocontrolled trapping of 3-phenylcyclopropene and its derivatives

AE Sheshenev, MS Baird, AK Croft…

Index: Sheshenev, Andrey E.; Baird, Mark S.; Croft, Anna K.; Bolesov, Ivan G. Mendeleev Communications, 2004 , vol. 14, # 6 p. 299 - 301

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Citation Number: 9

Abstract

Selective methods for the preparation of 3-phenylcyclopropene and its 1-substituted derivatives are provided. The parent cyclopropene is readily trapped in (3+ 2)-and (4+ 2)- cycloadditions that lead to exo-3-phenyl-1, 2-disubstituted cyclopropanes. Ab initio calculations suggest that the lowest energy conformation has the plane of the benzene ring perpendicular to the cyclopropene π-bond but with a low rotation barrier.