Manatt, Stanley L. and Vogel, Martin and Knutson, David and Roberts, John D. (1964) Small-Ring Compounds. XLII. Synthesis and Reactions of 3-Phenyl-2-cyclobutenone and Some Related Compounds. Journal of the American Chemical Society, 86 (13). pp. 2645-2653. ISSN 0002-7863. doi:10.1021/ja01067a026. https://resolver.caltech.edu/CaltechAUTHORS:20151015-110542043
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Abstract
Hydrogenation of either 1,1-difluoro-2,2-dichloro-3-phenylcyclobutane(VII) or 1,1-difluoro-2,2-dichloro-2-phenylcyclobutene (VI) over a palladium-on-charcoal catalyst gave 1,1-difluoro-3-phenylcyclobutane (V). Bromination of V- by N-bromosuccinimide produced 1,1-difluoro-3-bromo-3-phenylcyclobutane(IX) which on dehydrobromination by potassium hydroxide in ethanol afforded 1,1-difluoro-3-phenyl-2-cyclobutene(IV). Hydrolysis of IV by concentrated sulfuric acid gave 3-phenyl-2-cyclobutenone (I). Treatment of I with hot dilute aqueous base produced mixtures of benzoic acid, acetophenone, and benzoylacetone. The ring opening of I in boiling acetic acid gave β-methyl-trans-cinnamic acid. Catalytic hydrogenation of I produced 3-phenylcyclobutanone (XI). Sodium borohydride reduction of I afforded 3-phenyl-2-cyclobutenol (XII) which on catalytic hydrogenation gave cis-3-phenylcyclobutanol (XIII); XIII was also obtained by catalytic hydrogenation of 2-chloro-3-phenyl-2-cyclobutenol( XVI) from the sodium borohydride reduction of 2-chloro-3-phenyl-2-cyclobutenone (XV).
| Item Type: | Article | |||||||||
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| Additional Information: | © 1964 American Chemical Society. Received January 20, 1964. Presented in part at the Fourteenth National Organic Chemistry Symposium of the American Chemical Society, Lafayette, Ind., June, 1955, and at the 138th National Meeting of the American Chemical Society, New York, NY, Sept. 15, 1960, Abstracts of Papers, p 72P. Supported in part by the National Science Foundation. Monsanto Chemical Co Predoctoral Fellow, 1957-1958. | |||||||||
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| Issue or Number: | 13 | |||||||||
| DOI: | 10.1021/ja01067a026 | |||||||||
| Record Number: | CaltechAUTHORS:20151015-110542043 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151015-110542043 | |||||||||
| Official Citation: | Small-Ring Compounds. XLII. Synthesis and Reactions of 3-Phenyl-2-cyclobutenone and Some Related Compounds Stanley L. Manatt, Martin Vogel, David Knutson, and John D. Roberts Journal of the American Chemical Society 1964 86 (13), 2645-2653 DOI: 10.1021/ja01067a026 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61178 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 15 Oct 2015 20:00 | |||||||||
| Last Modified: | 10 Nov 2021 22:45 |
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