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
Full text is not posted in this repository. Consult Related URLs below.
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20151020-124113150
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).
| Item Type: | Article | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Related URLs: |
| |||||||||
| Additional Information: | © 1961 American Chemical Society. Received August 30, 1960. Supported in part by the National Science Foundation. General Electric Co. Fellow, 1957-1958. | |||||||||
| Funders: |
| |||||||||
| Other Numbering System: |
| |||||||||
| 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 |
Repository Staff Only: item control page
