Chlorofluoromethyl

ChLorofluorocarbene generated by the thermal decomposition of dichlorofluoro-methylphenylmercury reacts with 2,3-dimethylindole to give 3-fluoro-2,4-di-methylquinoline, 3-chloro-2,4-dimethylqumoline and 3-(chlorofluoromethyl)-2,3-dimethylindole [f] (equation 1). Similar results are obtained when the chloro-fluorocarbene is generated from dichlorofluoromethane by base-catalyzed de-hydrohalogenation using a phase-transfer catalyst in an aqueous-organic solvent system [21 (equation 1). 

The nucleophilic adduct 12 of benzimidazole to chlorotrifluoroethene is transformed to 4-(2-aminophenyl)-3-methyl-l,2,4-triazole (14) by a multistcp mechanism in its reaction with hydrazine hydrate 131 the last steps comprise the reduction of the chlorofluoromethyl group on the triazole ring (13). The overall reaction appears to be general.15 ... 

Reaction of ethyl chlorofluoroacetate with phenylmagnesium bromide at -50° affords U, a ketone, chlorofluoromethyl phenyl ketone. Treatment... 

Although free trifluoromethyl cation salts have not yet been isolated and characterized, it is possible to generate a mixture of chlorofluoromethyl cations (CFyClj., ) in situ from carbon tetrachloride and strong Lewis acids [8]. These systems can be used for electrophilic trihalomethylation of electron-rich aromatic substrates. The remaining chlorine substituents are substituted by fluorine with 70% HF-pyridine (Scheme 2.141). 

Chlorofluoromethyl radical CCIF-H 74.0 4 309.6 16.7 Derived This volume... 

A suspension of benzaldehyde and chlorofluoromethyl phenyl ketone in Na2CO,/ NaHC03 buffer soln. (pH 11) containing bovine serum albumin stirred at room temp, for 72 h - product. Y 74% (84% Z). F.e. incl. ester derivs. s. T. Kitazume, T. Ikeya, Chem. Express 4, 81-4 (1989). 

Apparently, since their development in the early 1930s by the E.I. duPont Company, the increasing use of these materials has proved to be deleterious to the ozone (O3) present in the upper atmosphere. It is now widely held that the photochemical destruction of the CFCs results in the production of chlorine atoms (-Cl) and chlorofluoromethyl radicals (e.g., CCIF2) (Equation 7.3) and the former, among... 

When chlorofluoromethyl ions react with benzene or toluene. It Is seen that HCl elimination strongly predominates over HF elimination In reactions analogous to 69-71. 

Haas, A., Terfluoropseudohalides and the Chemistry of Chlorofluoromethyl-sulfenyl Compounds," In New Pathways Inorg. Chem. Ebsworth, E. A. V., Ed. University Press Cambridge, England, 1968 p 87. 

Maddock, and A. G. Sharpe, C.U.P., 1968 [see the chapters entitled Perfluoropseudohalides and the Chemistry of Chlorofluoromethyl-sulphenyl Compounds (A. Haas) Polyfluoroalkyl Silicon Compounds (R. N. Haszeldine) Fluoroalkylmercurials (J. J. Lagowski)]. 

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