Small-Ring Compounds. XXXI. Cyclobutane Derivatives from Adducts of Cyclohexenylacetylene and Fluorochloroethylenes
- Creators
- Sharts, Clay M.
- Roberts, John D.
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).
Additional Information
© 1961 American Chemical Society. Received August 30, 1960. Supported in part by the National Science Foundation. General Electric Co. Fellow, 1957-1958.Additional details
- Eprint ID
- 61331
- DOI
- 10.1021/ja01465a032
- Resolver ID
- CaltechAUTHORS:20151020-124113150
- NSF
- General Electric
- Created
-
2015-10-20Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and Crellin Laboratories of Chemistry
- Other Numbering System Identifier
- 2611