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Small-Ring Compounds. XI. Some New Cyclobutane, Cyclobutene and Cyclobutanone Derivatives Derived from the Adduct of Phenylacetylene with 1,1-Difluoro-2,2-dichloroethylene

Roberts, John D. and Kline, G. Bruce and Simmons, Howard E., Jr. (1953) Small-Ring Compounds. XI. Some New Cyclobutane, Cyclobutene and Cyclobutanone Derivatives Derived from the Adduct of Phenylacetylene with 1,1-Difluoro-2,2-dichloroethylene. Journal of the American Chemical Society, 75 (19). pp. 4765-4768. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151022-111327031

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Abstract

The adduct (I) of phenylacetylene and 1,1-difluoro-2,2-dichloroethylene (obtained in 76% yield in 2 hours at 130º) has been shown to be 1,1-difluoro-2,2-dichloro-3-phenylcyclobutene. Hydrogenation of I yielded1,1-difluoro-3-phenylcyclobutane (II), while hydrolysis with concentrated sulfuric acid at 100º gave crystalline 2,2-dichloro-3-phenylcyclobutenone (III). The structure of III was firmly established by base-induced cleavage to 4,4-dichloro-3-phenyl-2-butenoic acid (IV) and by reduction to 3-phenylcyclobutanone. I was found to rearrange to 1,1-difluoro-2,4-dichloro-3-phenylcyclobutene (VIII) on heating with triethylamine. VIII on hydrolysis with concentrated sulfuric acid yielded 2,4-dichloro-3-phenylcyclobutenone (IX), the structure of which was established by reactions similar to those used for III and reduction to phenylcyclobutane. IX displayed no tendency to yield 1-acetoxy-2,4-dichloro-3-phenylcyclobutadiene with isopropenyl acetate and p-toluenesulfonic acid under conditions where other ketones are converted to enol acetates.


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http://dx.doi.org/10.1021/ja01115a044DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01115a044PublisherArticle
Additional Information:© 1953 American Chemical Society. Received March 9, 1953. We are indebted to Dr. M. Tsutsui and Mr. David Knutson for help with some of the experimental work.
Record Number:CaltechAUTHORS:20151022-111327031
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151022-111327031
Official Citation:Small-Ring Compounds. XI. Some New Cyclobutane, Cyclobutene and Cyclobutanone Derivatives Derived from the Adduct of Phenylacetylene with 1,1-Difluoro-2,2-dichloroethylene John D. Roberts, G. Bruce Kline, and Howard E. Simmons Jr. Journal of the American Chemical Society 1953 75 (19), 4765-4768 DOI: 10.1021/ja01115a044
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61411
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 18:53
Last Modified:22 Oct 2015 18:53

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