Journal of the American Chemical Society p. 7764 - 7768 (1981)
Update date:2022-08-11
Topics:
Dannenberg
Goldberg
Barton
Dill
Weinwurzel
Longas
The solvolyses of CH3CH2CH(OTs)CH3, CH3CH2CD(OTs)CD3 (III) and CD3CD2CH(OTs)CH3 (XIII) have been studied in CF3COOH and CF3COOD. The product distributions and solvolysis rates are consistent with the intermediacy of a hydrogen-bridged 2-butyl cation. The ratio of the solvolysis rates of III to XIII is 1.1-1.2 which is consistent with anchimeric assistance by a β-H on C3. The rate of additions of CF3COOH to 2-butene is less than half as fast as the trifluoroacetolysis, thereby eliminating 2-butene as an intermediate in the reaction. The steady-state concentration of 2-butene is shown to be proportional to added [CF3COONa], indicating that the trifluoroacetate anion, often used as a buffer, is a strong enough base to direct the reaction toward elimination products.
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