Rc. Gatrone et Sd. Jonson, THE INFLUENCE OF RADICAL STABILITY OF ORGANOMAGNESIUM HALIDE REAGENTSON THE DIRECTION OF ADDITION TO AN ALPHA,BETA-UNSATURATED PHOSPHORYL GROUP, Synthetic communications, 23(19), 1993, pp. 2743-2751
The addition of Grignard reagents with increasing radical character to
alpha,beta-unsaturated phosphoryl groups was found to occur with a co
rresponding increase in the yield of the aromatic substitution product
s. Molecular modelling was used to determine that the radical characte
r has a greater role in determining the degree of aromatic substitutio
n than does steric parameters.