RADICAL REDUCTION OF C-Cl BONDS IN CHLOROFLUORO ETHERS

Article abstract of DOI:10.1135/cccc19930565

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, tetrahydrofuran, diethyl ether, 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-trifluoroethyl chloromethyl ether (V) - it was also possible to prove the formation of 1,2-dichloro-1,2-bis(2-chloro-1,1,2-trifluoroethoxyethane) (VI), 1-chloro-1,2-bis(2-chloro-1,1,2-trifluoroethoxy)ethene (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 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.