Journal of the American Chemical Society p. 2895 - 2901 (1984)
Update date:2022-08-31
Topics:
Kevill, Dennis N.
Bahari, Mohd. S.
Anderson, Steven W.
The solvolysis of 2-adamantyl perchlorate proceeds at a convenient rate at temperatures close to ambient in a wide variety of pure and aqueous organic solvents.The nucleofugality of the perchlorate ion in SN1 reactions is shown to be several orders of magnitude higher than for more conventional leaving groups, such as p-toluenesulfonate or bromide.Entropies of activation in pure organic solvents nd in 80percent ethanol are unusually high.Grunwald-Winstein plots are markedly curved, with deviations being especially marked for aqueous-acetone and aqueous-2,2,2-trifluoroethanol mixtures.A scale of YOClO3 values is developed and compared with scales for a variety of other leaving groups.In aqueous ethanol there is a preference for product formation by interaction with water molecules by a factor of ca. 1.7, essentially independent of solvent composition (96-50percent ethanol) and temperature.
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