Journal of Organic Chemistry p. 3514 - 3517 (1994)
Update date:2022-08-03
Topics:
Venkatesan, Hariharan
Greenberg, Marc M.
Modulation of the cyclopropylmethyl (CPM)/homoallyl radical equilibrium by phenyl substitution at the radical center is exploited in determining the kinetic versus thermodynamic preference for bond scission in a bicyclic CPM radical.Exocyclic ring opening is determined to be 28.7 times faster than the respective endocyclic process.This method will be of general use for determining the regioselectivity of radical rearrangements.
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