865351-09-3Relevant articles and documents
Generation and stereocontrolled trapping of 3-phenylcyclopropene and its derivatives
Sheshenev, Andrey E.,Baird, Mark S.,Croft, Anna K.,Bolesov, Ivan G.
, p. 299 - 301 (2004)
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.
Generation and stereoselective transformations of 3-phenylcyclopropene
Sheshenev, Andrey E.,Baird, Mark S.,Croft, Anna K.,Bolesov, Ivan G.
experimental part, p. 10036 - 10046 (2010/02/27)
A convenient and inexpensive approach to the generation of 3-phenylcyclopropenes is described. Reaction of these compounds with a range of dienophiles and dipolarophiles led to the stereoselective formation of [4+2]- and [3+2]-cycloadducts, which were exclusively exo-3-phenyl-cis-1,2-disubstituted cyclopropanes. Efficient trapping of 1-lithio-3-phenylcyclopropene with different electrophiles is also discussed. Ab initio calculations suggest that the lowest energy conformation of 3-phenylcyclopropene has the plane of the benzene ring perpendicular to the cyclopropene π-bond but with a low rotation barrier.
