Journal of Organometallic Chemistry p. 9 - 14 (1993)
Update date:2022-08-04
Topics:
Hill, E. Alexander
Li, Baoju
The kinetics of the ring-cleavage rearrangements of 1-phenylcyclobutylmethylmagnesium chloride and its p-methyl and p-chloro analogs have been determined.The first-order rate constants are correlated by the Hammett equation, with ρ=-0.47.The results are consistent with a concerted mechanism with a cyclic transition state having significant polar character, although polar effects on the stabilities of reactant and product may also contribute.The phenyl group itself slows the reaction by a factor of 0.031, which is interpreted principally in terms of steric destabilization of the transition state.
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Doi:10.1002/ejoc.200300274
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