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Allylic Rearrangements. XVIII. Coupling Reactions of Butenylmagnesium Bromide

Young, William G. and Roberts, John D. and Wax, Harry (1945) Allylic Rearrangements. XVIII. Coupling Reactions of Butenylmagnesium Bromide. Journal of the American Chemical Society, 67 (5). pp. 841-843. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20150930-135824067

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Abstract

In connection with our work on the nature of the butenyl Grigiiard reagent it was desirable to study the coupling reactions of butenylmagnesium bromide. Henne, Chanan and Turk have coupled butenyl chlorides in the presence of magnesium while Lespieau and Heitzmann have reported similar experiments with crotyl bromide, but the results of these investigators are not in agreement. Furthermore, it is not clear whether or not the butenyl Grignard reagent is truly involved under conditions where the organometallic compound couples as rapidly as it forms. Indeed, valuable information might be expected from a comparison of the products resulting from the rapid coupling of two halide molecules with magnesium and from the coupling of a preparation of the Grignard reagent with a suitable halide. We have, therefore, made a study of the coupling reactions of butenylmagnesium bromide. After the completion of this work a paper by Levy and Cope appeared describing a number of similar experiments but without comment as to the significance of the results.


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http://dx.doi.org/10.1021/ja01221a043DOIArticle
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Additional Information:© 1945 American Chemical Society. Received January 20, 1945. [John D. Roberts] Abbott Laboratories Research Fellow, 1943-1944.
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Abbott LaboratoriesUNSPECIFIED
Record Number:CaltechAUTHORS:20150930-135824067
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20150930-135824067
Official Citation:Allylic Rearrangements. XVIII. Coupling Reactions of Butenylmagnesium Bromide William G. Young, John D. Roberts, and Harry Wax Journal of the American Chemical Society 1945 67 (5), 841-843 DOI: 10.1021/ja01221a043
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60635
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:01 Oct 2015 22:55
Last Modified:02 Oct 2015 16:19

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