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. doi:10.1021/ja01174a032. 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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| Additional Information: | © 1949 American Chemical Society. Received October 13, 1948. | |||||||||
| Issue or Number: | 6 | |||||||||
| DOI: | 10.1021/ja01174a032 | |||||||||
| 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: | 10 Nov 2021 22:36 |
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