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

Young, William G. and Roberts, John D. (1945) The Butenes from the Reduction of Isobutyraldehyde by s-Butylmagnesium Bromide. Journal of the American Chemical Society, 67 (6). p. 1040. ISSN 0002-7863. doi:10.1021/ja01222a510.

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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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Additional Information:© 1945 American Chemical Society. Received December 5, 1944. [John D. Roberts] Abbott Laboratories Research Fellow, 1943-1944.
Funding AgencyGrant Number
Abbott LaboratoriesUNSPECIFIED
Issue or Number:6
Record Number:CaltechAUTHORS:20150930-135823808
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Official Citation:The Butenes from the Reduction of Isobutyraldehyde by s-Butylmagnesium Bromide William G. Young and John D. Roberts Journal of the American Chemical Society 1945 67 (6), 1040-1040 DOI: 10.1021/ja01222a510
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60634
Deposited By: George Porter
Deposited On:30 Sep 2015 23:11
Last Modified:10 Nov 2021 22:36

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