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Small-Ring Compounds. XXXI. Cyclobutane Derivatives from Adducts of Cyclohexenylacetylene and Fluorochloroethylenes

Sharts, Clay M. and Roberts, John D. (1961) Small-Ring Compounds. XXXI. Cyclobutane Derivatives from Adducts of Cyclohexenylacetylene and Fluorochloroethylenes. Journal of the American Chemical Society, 83 (4). pp. 871-878. ISSN 0002-7863. doi:10.1021/ja01465a032. https://resolver.caltech.edu/CaltechAUTHORS:20151020-124113150

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Abstract

Cycloadditions of 1-ethynylcyclohex-1-ene with trifluorochloroethylene and difluorodichloroethylene gave 1,1,2 trifluoro-2-chloro- (IV) and 1,1-difluoro-2,2-dichloro-3(cyclohex-1-enyl-cyclobutene (XI), respectively. Both IV and XI were hydrolyzed by sulfuric acid to the corresponding monoketones, 2-fluoro-2-chloro- and 2,2-dichloro-3-(cyclohex-1-enyl)-cyclobutenones. With iodide and ethoxide ions IV or XI appeared to give S_N2' displacement products. Diels-Alder adducts were obtained from IV and maleic anhydride or dicarbethoxyacetylene. The triethylamine-catalyzed rearrangement of XI at 150º gave 1,1 difluoro-2,4-dichloro-3-(cyclohex-1-enyl)-cyclobutene (XXXI), but at 180º an unexpected elimination rearrangement led to 2-fluoro-1,3-dichloro-5,6,7,8-tetrahydronaphthalene (XXXIII).


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http://dx.doi.org/10.1021/ja01465a032DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01465a032PublisherArticle
Additional Information:© 1961 American Chemical Society. Received August 30, 1960. Supported in part by the National Science Foundation. General Electric Co. Fellow, 1957-1958.
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General ElectricUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2611
Issue or Number:4
DOI:10.1021/ja01465a032
Record Number:CaltechAUTHORS:20151020-124113150
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151020-124113150
Official Citation:Small-Ring Compounds. XXXI. Cyclobutane Derivatives from Adducts of Cyclohexenylacetylene and Fluorochloroethylenes Clay M. Sharts and John D. Roberts Journal of the American Chemical Society 1961 83 (4), 871-878 DOI: 10.1021/ja01465a032
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61331
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 21:01
Last Modified:10 Nov 2021 22:47

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