Small-Ring Compounds. XLV. Influence of Vinyl and Phenyl Substituents on the Interconversion of Allylcarbinyl-Type Grignard Reagents

Abstract

Equilibration of the α and β positions in y,y-diphenylallylcarbinylmagnesium bromide was complete after 5 hr at room temperature. Less than 0.3% of the isomeric cyclopropylcarbinyl derivative, however, is in equilibrium with the ring-opened species. While reactions of the Grignard reagents normally expected to have anionic-type mechanisms were found to lead to allylcarbinyl products only, substantial amounts of cyclic products were formed with molecular oxygen.

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