Journal of Organometallic Chemistry

Cyclization of the Grignard reagent from 5-chloro-3-methyl-1-hexene; a reversible organomagnesium rearrangement

EA Hill, MM Myers

Index: Hill,E.A.; Myers,M.M. Journal of Organometallic Chemistry, 1979 , vol. 173, p. 1 - 13

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Abstract

Abstract The Grignard reagent from 5-chloro-3-methyl-1-hexene cyclized reversibly to form an equilibrium mixture with two stereoisomers of the 2, 4-dimethylcyclobutylmethyl-Grignard reagent. Equilibrium and rate constants for the opposing reactions have been evaluated at 80–100 and 100–120 C, respectively. Over this range, the equilibrium mixture favors the cyclic reagent by a ratio of about Full-size image (< 1 K)