Tetrahedron p. 3017 - 3028 (1996)
Update date:2022-09-26
Topics:
Jiang, Xi-Kui
Ji, Guo-Zhen
Xie, John Rong-Yuan
A rigorous procedure was applied to the measurement of the relative rates, i.e. k(r)(Y) = k(Y)/k(H) of trichloromethyl-bromo-addition reactions to fourteen p-Y-substituted phenylacetylenes (I-Y, with Y = F, Cl, Br, Me, t-Bu, OMe, SMe, SiMe3, CF3, CN, NO2, SOMe, COMe, and CO2Me). The reaction was run in cyclohexane under nitrogen antmosphere at 65 ± 0.5°C. All products were derived from the intermediate YC6H4C = CHCCl3 adduct radicals. Correlation analysis of these rate data seems to suggest that both a polar and a spin-delocalization effect are operating at the transition state.
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