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Small-Ring Compounds. XVIII. Alkali-induced Ring Opening of Some Phenylcyclobutenone Derivatives

Skattebøl, L. and Roberts, John D. (1958) Small-Ring Compounds. XVIII. Alkali-induced Ring Opening of Some Phenylcyclobutenone Derivatives. Journal of the American Chemical Society, 80 (15). pp. 4085-4088. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151020-153343000

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Abstract

Phenylcyclobutenedione (I) has been found to decompose by the action of alkali to benzylidenepyruvic acid (X) and benzaldehyde. Similarly 2-hydroxy-3-phenyl-2-cyclobutenone (V) yields benzylpyruvic acid (VII), and 4-hydroxy-3-phenylcyclobutenedione (XI) gives phenylpyruvic acid (XII) and 1,3-diphenylpropene (XIII). Possible reaction mechanisms for the formation of these substances are proposed.


Item Type:Article
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http://dx.doi.org/10.1021/ja01548a065DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01548a065PublisherArticle
Additional Information:© 1958 American Chemical Society. Received January 9, 1958. Supported in part by the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry2296
Issue or Number:15
Record Number:CaltechAUTHORS:20151020-153343000
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151020-153343000
Official Citation:Small-Ring Compounds. XVIII. Alkali-induced Ring Opening of Some Phenylcyclobutenone Derivatives L. Skattebøl and John D. Roberts Journal of the American Chemical Society 1958 80 (15), 4085-4088 DOI: 10.1021/ja01548a065
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61344
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:21 Oct 2015 19:40
Last Modified:03 Oct 2019 09:07

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