The Butenes from the Reduction of Isobutyraldehyde by s-Butylmagnesium Bromide

Abstract

Whitmore and George have shown that the reduction of diisopropyl ketone by a Grignard reagent involves hydrogen atoms attached to the beta-carbon atom of the Grignard reagent. If the Grignard reagent had no hydrogen atoms on the β-carbon, as with neopentylmagnesium chloride, no reduction was detected. It was pointed out that a correlation exists between the extent of reduction of diisopropyl ketone and the number and primary, secondary or tertiary character of the β-hydrogens of the Grignard reagents. It is difficult, however, to determine the relative reduction rates of the different classes of β-hydrogen atoms from data obtained with several Grignard reagents because the competing reactions of addition and enolization are also markedly influenced by structure.

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