Collect. Czech. Chem. Commun. 1996, 61, 1215-1222

Radical Addition of 2-Propanol to Trifluoroethylene. Preparation of Trifluoroethylene Oligomersfrom Chlorotrifluoroethylene Oligomers

Jiří Fikar, Petr Trška, Pavel Pech and František Liška

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6,Czech Republic


Photochemically initiated addition of 2-propanol to trifluoroethylene afforded the 1 : 1 adducts 3,3,4-trifluoro-2-methyl-2-butanol 1 and 3,4,4-trifluoro-2-methyl-2-butanol 2, as well as the 1 : 2 telomers 3,4,4,5,5,6-hexafluoro-2-methyl-2-hexanol 3 and 3,4,4,5,6,6-hexafluoro-2-methyl-2-hexanol 4. The other possible 1 : 2 and 1 : 3 telomers, in which the CF2-CFH- groups regularly alternate ("head-tail") - 3,3,4,5,5,6-hexafluoro-2-methyl-2-hexanol 13 and 3,3,4,5,5,6,7,7,8-nonafluoro-2-methyl-2-octanol 14 - and which did not arise in the reaction, were obtained by photochemical reduction of addition products of 2-propanol to chlorotrifluoroethylene (alcohols 15-17) with secondary and tertiary amines. Dehydrofluorination of alcohols 1 and 2 gave 3,3-difluoro-2, 2-dimethyloxetane 18 and 3-difluoromethyl-2,2-dimethyloxirane 19.

Keywords: Trifluoroethylene; 2-Propanol; Photoaddition to fluoroethylenes; Photoreduction of chlorofluoro compounds.