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. doi:10.1021/ja01115a044. https://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.
| Item Type: | Article | |||||||||
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| 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. | |||||||||
| Issue or Number: | 19 | |||||||||
| DOI: | 10.1021/ja01115a044 | |||||||||
| Record Number: | CaltechAUTHORS:20151022-111327031 | |||||||||
| Persistent URL: | https://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: | 10 Nov 2021 22:48 |
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