694-91-7Relevant articles and documents
Dynamic effects on [3,3] and [1,3] shifts of 6-methylenebicyclo[3.2.0]hept- 2-ene
Suhrada, Christopher P.,Selcuki, Cenk,Nendel, Maja,Cannizzaro, Carina,Houk,Rissing, Peter-Juergen,Baumann, Dirk,Hasselmann, Dieter
, p. 3548 - 3552 (2007/10/03)
(Figure Presented) Deuterium labeling experiments on the rearrangement of methylenebicycloalkene 1 to 3 show stereoselectivity despite the intermediacy of a stabilized diradical structure 2. A theoretical model built from computational studies explains the observed product ratios. Stereoselectivity among [3,3] (minor) products implicates an unusual bifurcation of reaction trajectories after the initial bond-breaking transition state.