Journal of the American Chemical Society p. 2121 - 2124 (1985)
Update date:2022-08-10
Topics:
Shiner, V. J.
Imhoff, Michael A.
Solvolysis of the title compound in ethanol-water, trifluoroethanol-water, and hexafluoroisopropyl alcohol-water mixtures yields > 90 percent products of methyl migration.The rate of solvolysis relative to the cyclopentyl analogue is 0.19 in 80 percent ethanol-water, 4.0 in 97 percent trifluoroethanol-water, and 10.0 in 90 percent hexafluoroisopropyl alcohol-water.The α-d and β-d2 rate effects in solvolysis range respectively from 1.19-1.20 to 1.26-1.30.The results are interpreted in terms of a mechanism which involves reversible formatin of the tight ion pair followed by rate-determining methyl migration.
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(1983)
