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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. http://resolver.caltech.edu/CaltechAUTHORS:20150930-135823808

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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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URLURL TypeDescription
http://dx.doi.org/10.1021/ja01222a510DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01222a510PublisherArticle
Additional Information:© 1945 American Chemical Society. Received December 5, 1944. [John D. Roberts] Abbott Laboratories Research Fellow, 1943-1944.
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Abbott LaboratoriesUNSPECIFIED
Record Number:CaltechAUTHORS:20150930-135823808
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20150930-135823808
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
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:30 Sep 2015 23:11
Last Modified:13 Feb 2019 18:03

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