Collection of Czechoslovak Chemical Communications - digital archive 

Abstract

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.