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Allylic Rearrangements. XXVI. The Reaction of Butenyl Mesitoates and Chlorides with Phenylmagnesium Bromide

Wilson, K. W. and Roberts, John D. and Young, William G. (1949) Allylic Rearrangements. XXVI. The Reaction of Butenyl Mesitoates and Chlorides with Phenylmagnesium Bromide. Journal of the American Chemical Society, 71 (6). pp. 2019-2020. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20150930-135819604

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Abstract

In 1941, Arnold, Bank and Liggett suggested that the formation of allylbenzene from the reaction of allyl mesitoate with phenylmagnesium bromide involved the combination of an intermediate allyl carbonium ion with a phenyl carbanion from the Grignard reagent. In a later paper this mechanism was modified since it was found that the reaction of crotyl mesitoate with phenylmagnesium bromide gave only crotylbenzene instead of the mixture of crotyl- and α-methylallylbenzenes expected from an intermediate butenyl carbonium ion. The exclusive formation of crotylbenzene was formulated as being the result of a concerted process involving a cyclic intermediate.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/ja01174a032DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01174a032PublisherArticle
Additional Information:© 1949 American Chemical Society. Received October 13, 1948.
Issue or Number:6
Record Number:CaltechAUTHORS:20150930-135819604
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150930-135819604
Official Citation:Allylic Rearrangements. XXVI. The Reaction of Butenyl Mesitoates and Chlorides with Phenylmagnesium Bromide K. W. Wilson, John D. Roberts, and William G. Young Journal of the American Chemical Society 1949 71 (6), 2019-2020 DOI: 10.1021/ja01174a032
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60619
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:02 Oct 2015 18:24
Last Modified:03 Oct 2019 08:58

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