Collect. Czech. Chem. Commun. 1993, 58, 565-574

Radical Reduction of C-Cl Bonds in Chlorofluoro Ethers

František Liška, Jiří Fikar and Petr Kuzmič

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


Reduction of C-Cl bonds in 2,2-dichloro-1,1,2-trifluoroethyl trichloromethyl ether (I), 2-chloro-1,1,2-trifluoroethyl trichloromethyl ether (II), and 2,2-dichloro-1,1,2-trifluoroethyl dichloromethyl ether (III) with 2-propanol, 2-butanol, cyclohexanol, tetrahydrofurane, diethyl ether, and 1,3-dioxolane initiated photochemically and by radiation has been investigated. Beside the main reduction products - 2-chloro-1,1,2-difluoroethyl trichloromethyl ether (IV) and 2-chloro-1,1,2-difluoroethyl chloromethyl ether (V) - it was also possible to prove the formation of 1,2-dichloro-1,2-bis(2-chloro-1,1,2-trifluoroethoxy)ethane (VI), 1-chloro-1,2-bis(2-chloro-1,1,2-trifluoroethoxy)ethane (VII), and 1,2-dichloro-1,2-bis(2-chloro-1,1,2-trifluoroethoxy)ethene (VIII). The structure of products was confirmed by elemental analysis, MS, IR, 1H NMR and 19F NMR spectra and by GLC comparison of the elution times with those of standards. The relative reduction ability of the solvents used in the reduction rate order of C-Cl bonds in the compounds (CCl3 > CFCl2 > CHCl2 and CFClH) are given.