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Small Ring Compounds. XXII. Ring Opening of Halogenated 3-Phenylcyclobutenones in Acetic Acid and Aqueous Sodium Hydroxide

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. 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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01554a065DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01554a065PublisherArticle
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.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
NSF Postdoctoral FellowshipUNSPECIFIED
Caltech Arthur A. Noyes FellowshipUNSPECIFIED
Fulbright FoundationUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry2350
Issue or Number:21
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:03 Oct 2019 09:06

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