Tetrahedron p. 8479 - 8490 (1997)
Update date:2022-08-30
Topics:
Jiang, Xi-Kui
Ding, William Fa-Xiang
Zhang, Yu-Huang
The relative rates [k(R)(Y) values] of bromine-atom abstraction reactions of 13 p-Y-substituted benzyl bromides (1Y's : Y = H, Et, tBu, Me3Si, MeS, Ph, P, Cl, Br, CF3, CN, CO2Me,SO2Me) by tris(trimethylsilyl) silyl radicals [(Me3Si)3Si.] in cyclohexane at 80°C have been measured by a rigorous methodology. Correlation analysis of the kinetic data by the dual-parameter equation (log k(H)/k(H) = ρ(x)σ(x)+ρ.σ.) shows that the silyl radical is distinctly nucleophilic and the transition states of the bromine-atom abstraction reactions are affected by both the polar and spindelocalization effects of the Y-substituents. Comparison of the |ρ(p) / ρ(jj).| values suggests that the contribution of the spin-delocalization effects in this Br-atom abstraction reaction may be greater than the spin-delocalization effects in some H-atom abstraction reactions.
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