Addition of 1,2-dibromo-1-chlorotrifluoroethane to chlorotrifluoroethylene induced by uv-radiation. Synthesis of perfluoro-1,3-butadiene and perfluoro-1,3,5-hexatriene
Abstract
Photochemically initiated reaction of 1,2-dibromo-1-chlorotrifluoroethane (II) with chlorotrifluoroethylene (I) gave 38% 1,4-dibromo-2,3-dichlorohexafluorobutane (III) and 19% 1,6-dibromo-2,3,5-trichlorononafluorohexane (IV) in addition to the higher telomers. Dehalogenations of III and IV yielded perfluoro-1,3-butadiene (VI) and perfluoro-1,3,5-hexatriene (VIII) with 3-chlorononafluoro-1,5-hexadiene (VII), respectively. Photochemical reduction of butane III with 2-propanol resulted in a preferential reduction of CBr bonds, and from 2,3-dichloro-1,1,2,3,4,4-hexafluorobutane (IX) thus formed, esters of difluoroacetic acid were prepared by dehalogenation of IX and subsequent oxidation and esterification of the product. The photochemical reduction of hexane IV gave a mixture of 79% trichlorononafluorohexane XII and 21% dichlorononafluorohexane XIII. The mechanism of formation of the unusual products of the title addition reaction is discussed.
- Publication:
-
Journal of Fluorine Chemistry
- Pub Date:
- January 1986
- DOI:
- 10.1016/S0022-1139(00)81263-4
- Bibcode:
- 1986JFluC..31..363D