Journal of Fluorine Chemistry p. 173 - 178 (1996)
Update date:2022-08-31
Topics:
Jiang, Xi-Kui
Ji, Guo-Zhen
Wang, Daniel Ze-Rong
para-Trifluorovinyl α,β,β-trifluorostyrene (1-CF=CF2), p-acetoxy α,β,β-trifluorostyrene (1-AcO) and p-vinyl α,β,β-trifluorostyrene (1-CH=CH2) have been synthesized. The rate constants (k) for the thermal cyclodimerization of 1-CF=CF2 and 1-AcO have been measured over the temperature range 90-130 °C for 1-CF=CF2 and 110-160 °C for 1-AcO. The σmb polar substituent constants of the p-CF=CF2, p-CH=CH2 and p-AcO groups calculated from the 19F NMR chemical shifts are: for p-CF=CF2, 0.40; for p-CH=CH2, 0.03; and for p-AcO, -0.14, and the σ JJ? spin-delocalization substituent constants of the p-CF=CF2 and p-AcO groups are 0.86 and 0.35, respectively, i.e., the former is a highly effective spin-stabilizer while the latter is moderately effective. Owing to the occurrence of a small amount of side-reaction, the σ JJ? value of the p-CH=CH2 group could not be accurately measured, but it was very roughly estimated to be in the range of 0.50-0.66.
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