Chemistry Letters, Vol.30, No.8, 806-807, 2001
Solvolysis of optically active 4-methylcyclohexylidenemethyl triflate: Evidence against a primary vinyl cation as an intermediate
Solvolysis of (R)-4-methylcyclohexylidenemethyl triflate in aqueous methanol at 140 degreesC gave stereospecifically (R)-4-methyl-cycloheptanone to definitively rule out intermediate formation of the achiral primary vinyl cation. The rearrangement must occur via concerted a-bond participation.