180578-10-3Relevant articles and documents
Stereochemistry of the thermal isomerizations of trans-1-ethenyl-2-phenylcyclopropane to 4-phenylcyclopentene
Baldwin, John E.,Bonacorsi Jr., Samuel J.
, p. 8258 - 8265 (2007/10/03)
The stereochemical course of the thermal isomerization of trans-1-ethenyl-2-phenylcyclopropane to 4-phenylcyclopentene at 216.4°C in the gas phase has been uncovered through syntheses and kinetic studies based on chiral d9-labeled analogs. This example of the vinylcyclopropane-to-cyclopentene rearrangement takes place with the participation of all four stereochemically distinct paths, the relative contributions (± 3%) being 58% si, 8% ar, 24% sr, and 10% ai. The stereochemical outcome is determined by alternative diradical transition structures of comparable energy, rather than by orbital symmetry control.
