Abstract
AbstractSolvolysis of (R)‐4‐methylcyclohexylidenemethyl triflate (6) was examined at 140 °C in various aqueous methanol and some other alcoholic solvents. The main product was (R)‐4‐methylcycloheptanone that maintains the stereochemical purity of 6, with accompanying 4‐methylcyclohexanecarbaldehyde. In the presence of bromide ion, the bromide substitution product was also obtained, mostly with inversion of configuration. It is concluded that the solvolysis does not involve the formation of the primary vinyl cation but proceeds via σ‐bond participation to form the rearranged cycloheptenyl cation as an intermediate. Copyright © 2002 John Wiley & Sons, Ltd.
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