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. doi:10.1021/ja01463a034. https://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.
Item Type: | Article | |||||||||
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Additional Information: | © 1961 American Chemical Society. Received August 4, 1960. Supported in part by the National Science Foundation. | |||||||||
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Issue or Number: | 2 | |||||||||
DOI: | 10.1021/ja01463a034 | |||||||||
Record Number: | CaltechAUTHORS:20151020-124114951 | |||||||||
Persistent URL: | https://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: | 10 Nov 2021 22:47 |
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