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Allylic Rearrangements. XX. Some Addition Reactions of Butenylmagnesium Bromide

Young, William G. and Roberts, John D. (1946) Allylic Rearrangements. XX. Some Addition Reactions of Butenylmagnesium Bromide. Journal of the American Chemical Society, 68 (4). pp. 649-652. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20150930-135822455

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Abstract

Preceding studies of the butenyl Grignard reagent have indicated a striking tendency on the part of the reagent to introduce an α-methylallyl group in coupling reactions with allylic chlorides and in addition reactions to aldehyde, ketones and carbon dioxide. Even with highly-hindered ketones as diisopropyl ketone and acetomesitylene the reaction products are predominantly α-methylallyl derivatives. We have now turned to the investigation of other types of addition reactions of butenylmagnesium bromide and find that with phenyl isocyanate, ethyl formate arid ethyl orthoformate the reaction products correspond almost exclusively to the secondary form of the Grignard reagent. With ethyl orthoformate some ( <4%) of the diethyl acetal of 3-pentenal was obtained but in the other reactions none of the products resulting from the introduction of the primary butenyl group by the Grignard reagent was detected.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01208a037DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01208a037DOIArticle
Additional Information:© 1946 American Chemical Society. Received September 27, 1945. [John D. Roberts] Abbott Laboratories Research Fellow, 1943-1944.
Funders:
Funding AgencyGrant Number
Abbott LaboratoriesUNSPECIFIED
Issue or Number:4
Record Number:CaltechAUTHORS:20150930-135822455
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150930-135822455
Official Citation:Allylic Rearrangements. XX. Some Addition Reactions of Butenylmagnesium Bromide William G. Young and John D. Roberts Journal of the American Chemical Society 1946 68 (4), 649-652 DOI: 10.1021/ja01208a037
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60629
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:05 Oct 2015 17:22
Last Modified:03 Oct 2019 08:58

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