Silversmith, Ernest F. and Kitahara, Yoshio and Caserio, Marjorie C. and Roberts, John D. (1958) Small Ring Compounds. XXII. Ring Opening of Halogenated 3-Phenylcyclobutenones in Acetic Acid and Aqueous Sodium Hydroxide. Journal of the American Chemical Society, 80 (21). pp. 5840-5845. ISSN 0002-7863. doi:10.1021/ja01554a065. https://resolver.caltech.edu/CaltechAUTHORS:20151020-141343438
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Abstract
Ring-opening reactions of a number of halogen-substituted 3-phenylcyclobutenones in acetic acid and in aqueous sodium hydroxide have been investigate and the resulting carboxylic acids identified. The course of reaction in acetic acid can be rationalized by a mechanism involving vinylketene intermediates. The base-induced ring-opening reaction appears to follow a course dependent on the number and location of the halogen atoms but is generally similar to the haloform reaction.
| Item Type: | Article | ||||||||||
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| Additional Information: | © 1958 American Chemical Society. Received May 22, 1958. Supported in part by a grant from the National Science Foundation; National Science Foundation Postdoctoral Fellow, 1955-1956; Arthur A. Noyes Fellow, 1966-1957. Fulbright travel grantee. | ||||||||||
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| Issue or Number: | 21 | ||||||||||
| DOI: | 10.1021/ja01554a065 | ||||||||||
| Record Number: | CaltechAUTHORS:20151020-141343438 | ||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151020-141343438 | ||||||||||
| Official Citation: | Small Ring Compounds. XXII. Ring Opening of Halogenated 3-Phenylcyclobutenones in Acetic Acid and Aqueous Sodium Hydroxide Ernest F. Silversmith, Yoshio Kitahara, Marjorie C. Caserio, and John D. Roberts Journal of the American Chemical Society 1958 80 (21), 5840-5845 DOI: 10.1021/ja01554a065 | ||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||
| ID Code: | 61341 | ||||||||||
| Collection: | CaltechAUTHORS | ||||||||||
| Deposited By: | Ruth Sustaita | ||||||||||
| Deposited On: | 20 Oct 2015 21:58 | ||||||||||
| Last Modified: | 10 Nov 2021 22:47 |
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