Relative Reactivities of Styrene, α,β,β-Trifluorostyrene and Phenylacetylene toward Attacks of Trichloromethyl Radicals as measured by Direct Competition between the Substrates

Abstract

The relative rates of the addition of trichloromethyl radicals to styrene, α,β,β-trifluorostyrene and phenylacetylene in cyclohexane at 65 °C, measured by a direct competition procedure, are 1:0.23:0.40.

References

1. S. W. Benson, J. Chem. Educ., 1965, 42, 502.
2. (a) D. T. Clark, Chem. Commun., 1966, 390; (b) P. Politzer and J. W. Timberlake, J. Org. Chem., 1972, 37, 3557.
3. D. C. Nonhebel and J. C. Walton, Free-radical Chemistry, Cambridge University Press, Cambridge, 1974, (a)p. 225; (b)222.
4. G. E. Owen, Jr., J. M. Pearson and M. Szwarc, Trans. Faraday Soc., 1965, 61, 1722.
5. (a) S. P. Skell and A. Y. Garner, J. Am. Chem. Soc., 1956, 78, 5430; (b) G. A. Russell, in Investigation of Rates and Mechanisms of Reactions, ed. S. L. Friess, E. S. Lewis and Weissberger, Interscience, New York, 1961, pp. 343–344.
6. J. M. Pearson and M. Szwarc, Trans. Faraday Soc., 1964, 60, 553.
7. J. M. Tedder and J. C. Walton, Trans. Faraday Soc., 1964, 60, 1769.
8. (a) G. H. X. Guo, S. S. Sun, G. Z. Ji and X. K. Jiang, J. Chem. Res., 1993, (S) 166; (M) 1123; (b) X. K. Jiang, W. W. Z. Liu and S. H. Wu, J. Phys. Org. Chem., 1994, 7, 96; (c) X. K. Jiang, G. Z. Ji and J. R. Y. Xie, Tetrahedron, 1996, 52, 3017; (d) X. K. Jiang, Y. H. Zhang and W. F. X. Ding, J. Chem. Soc., Perkin Trans. 2, 1996, 1391.
9. (a) X. K. Jiang and G. Z. Ji, J. Org. Chem., 1992, 57, 6051.
10. X. K. Jiang, G. Z. Ji and C. X. Yu, Huaxue Xuebao, 1986, 44, 72; Acta Chim. Sin. (Engl. Ed.), 1985, 369.