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Small-Ring Compounds. XLII. Synthesis and Reactions of 3-Phenyl-2-cyclobutenone and Some Related Compounds

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. http://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).


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http://dx.doi.org/10.1021/ja01067a026DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01067a026PublisherArticle
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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NSFUNSPECIFIED
Monsanto CorporationUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry3051
Record Number:CaltechAUTHORS:20151015-110542043
Persistent URL:http://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:15 Oct 2015 20:00

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