Solvolysis of vinyl triflates. Effect of alkyl substituents, solvents, and added nucleophiles

RH Summerville, CA Senkler…

Index: Summerville,R.H. et al. Journal of the American Chemical Society, 1974 , vol. 96, p. 1100 - 1110

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Citation Number: 42

Abstract

Abstract: Vinyl solvolyses are somewhat anomalous when compared with the behavior of saturated analogs. There is evidence of nucleophilic solvent involvement of alkyl-substituted vinyl substrates (m and l values are of intermediate magnitude and the effect of changes in solvent nucleophilicity at constant ionizing power is significant), but, in contrast, the carbonium ion character is high (p* is large for alkyl substitution) and added strong ...