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:

URL	URL Type	Description
http://dx.doi.org/10.1021/ja01554a065	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ja01554a065	Publisher	Article

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 Agency	Grant Number
NSF	UNSPECIFIED
NSF Postdoctoral Fellowship	UNSPECIFIED
Caltech Arthur A. Noyes Fellowship	UNSPECIFIED
Fulbright Foundation	UNSPECIFIED

Other Numbering System:

Other Numbering System Name	Other Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry	2350

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CaltechAUTHORS:20151020-141343438

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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

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ID Code:

61341

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CaltechAUTHORS

Deposited By:

Ruth Sustaita

Deposited On:

20 Oct 2015 21:58

Last Modified:

03 Oct 2019 09:06

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