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Small-Ring Compounds. XXX. Reactions of Phenylcyclobutadienoquinone with Methanol

Mallory, Frank B. and Roberts, John D. (1961) Small-Ring Compounds. XXX. Reactions of Phenylcyclobutadienoquinone with Methanol. Journal of the American Chemical Society, 83 (2). pp. 393-397. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151020-124114951

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Abstract

The thermal reaction of phenylcyclobutadienoquinone (I) with methanol gives 2,4-dimethoxy-3-phenylcyclobutenone The relative A possible mechanism is presented that accounts for the 2-hydroxy-2-methoxy-3-phenylcyclobutenon(IV). (II), 3-phenyl-4-hydroxy-4-methoxy-2-butenoiaccid lactone (III) and dimethyl phenylsuccinate (IV). The relative yields of the three products depend on the reaction temperature. A possible mechanism is presented that accounts for the formation of the three products by way of a common intermediate: 2-hydroxy-2-methoxy-3-phenylcyclobutenone (V). The structures of II and III were established by spectroscopic analysis, chemical degradation and independent synthesis.


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http://dx.doi.org/10.1021/ja01463a034DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01463a034PublisherArticle
Additional Information:© 1961 American Chemical Society. Received August 4, 1960. Supported in part by the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry2497
Record Number:CaltechAUTHORS:20151020-124114951
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151020-124114951
Official Citation:Small-Ring Compounds. XXX. Reactions of Phenylcyclobutadienoquinone with Methanol Frank B. Mallory and John D. Roberts Journal of the American Chemical Society 1961 83 (2), 393-397 DOI: 10.1021/ja01463a034
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61333
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 20:56
Last Modified:20 Oct 2015 20:56

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