Small-Ring Compounds. XLIV. Interconversion of Cyclopropylcarbinyl and Allylcarbinyl Grignard Reagents

Abstract

The previously postulated rapid conversion of the cyclopropylcarbinyl Grignard reagent to the allylcarbinyl Grignard reagent has been confirmed by partial trapping of cyclopropylcarbinylmagnesium chloride prepared in refluxing diethyl ether in the presence of benzoic acid as methylcyclopropane and formation of cyclopropylcarbinylmagnesium bromide at - 24º from the corresponding bromide and magnesium in dimethyl ether. The rearrangement of cyclopropylcarbinylmagnesium bromide to allylcarbinylmagnesium bromide appears to be a first-order reaction and has a half-life of 121 min. at -24º.

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