RADICAL REDUCTION OF C-CL BONDS IN CHLOROFLUORO ETHERS

Reduction of C-Cl bonds in 2,2-dichloro-1,1.2-trifluoroethyl trichloro methyl ether (1). 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, tetrahydrofuran, diethyl et her. and 1,3-dioxolane initiated photochemically and by radiation has been investigated. Beside the main reduction products - 2-chloro-1,1,2 -trifluoroethyl dichloromethyl ether (IV) and 2-chloro-1.1.2-trifluoro ethyl chloromethyl ether (V) - it was also possible to prove the forma tion of loro-1,2-bis(2-chloro-1,1,2-trifluoroethoxy)ethane (VI). loro- 1,2-bis(2-chloro-1,1,2-trifluoroethoxy)ethene (VII), and 2-dichloro-1. 2-bis(2-chloro-1,1,2-trifluoroethoxy) ethene (VIII). The structure of products was confirmed by elemental analysis, MS, IR, H-1 NMR and F-19 NMR spectra and by GLC comparison of the elution times with those of the standards. The relative reduction ability of the solvents used and the reduction rate order of C-Cl bonds in the compounds (CCl3 > CFCl2 > CHCl2 and CFClH) are given.