THE 1,2-FLUORINE ATOM MIGRATION IN THE EPOXIDE OF 1,1-DICHLORODIFLUOROETHENE. THE INFRARED SPECTRUM OF DICHLOROFLUOROACETYL FLUORIDE

Article abstract of DOI:10.1016/S0022-1139(00)82372-6

The epoxide of 1,1-dichlorodifluoroethene, , and chlorodifluoroacetyl chloride, CF2ClC(O)Cl, were the principle products of the gas-phase thermal reaction of NO2 with 1,1-dichlorodifluoroethene, CF2CCl2, in presence of O2 at 257.3 K and 300.2 deg K.Five other products: COF2, COCl2, O2NCF2C(O)Cl, CF2ClCCl2NO2 and CF2ClCCl2O2NO2 were also formed in minor amounts of traces, depending on the relation between NO2, CF2Cl2 and O2.The initial pressure of NO2 was varied between 0.7 and 4.7 torr, that of CF2CCl2 between 18.4 and 81.9 torr, and that of O2 between 50.4and 696.3 torr.The isomerisation of to CF2ClC(O)Cl was never observed, but, in the presence of mercury vapour, the rearrangement of to CFCl2C(O)F occured, involving the unexpected 1,2-migration of a fluorine atom.The infrared spectrum of CFCl2C(O)F is given.The elementary reactions sequence is proposed to explain the formation of CF2C(O)Cl and .