The Influence of Radical Stability of Organomagnesium Halide Reagents on the Direction of Addition to an α-β-Unsaturated Phosphoryl Group

Abstract

The addition of Grignard reagents with increasing radical character to α,β-unsaturated phosphoryl groups was found to occur with a corresponding increase in the yield of the aromatic substitution products. Molecular modelling was used to determine that the radical character has a greater role in determining the degree of aromatic substitution than does steric parameters.