Journal of the American Chemical Society p. 1098 - 1103 (1988)
Update date:2022-08-16
Topics:
Petris, Giulia de
Giacomello, Pierluigi
Pizzabiocca, Adriano
Renzi, Gabriele
Speranza, Maurizio
The gas-phase pinacol rearrangement of cis- and trans-1,2-dimethylcyclohexane-1,2-diols, promoted by D3+, CH5+/C2H5+ and t-C4H9+ ions, was studied by mass spectrometric and radiolytic methods in the pressure range 0.5-760 Torr.When product isomerization is inhibited, by using N(CH3)3 as a trapping reagent at high pressure, mixtures of 2,2-dimethylcyclohexanone and 1-acetyl-1-methylcyclopentane were recovered from the reaction.In methane, the trend of measured relative rates for ring contraction (k5), methyl or hydroxyl group migration (k6) versus the rearrangement rate of pinacol itself (kp), is k6(trans) = k5(trans) > k5(cis) > k6(cis) > kp.No evidence for the formation of an intermediate carbenium ion was found.Stereochemical aspects of the mechanism are discussed and compared with solution data.
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