FLUORINATED ORGANOLITHIUM COMPOUNDS

See Other FLUORINATED ORGANOLITHIUM compound f2060. Hexafluorobenzene... 

This compound was found, on investigation of an explosion in a syringe during transfer, to have a decomposition energy equivalent to that of commercial explosives. Slow decomposition, even at room temperature, becomes explosive above 100°C. Shock sensitive. Stable as hydrocarbon solution below 25% concentration. Recommended that this and related compounds be handled only in such solution. See FLUORINATED ORGANOLITHIUM COMPOUND... 

The intermediate fluorinated organolithium compounds display limited stability at low temperature, but can be transmetalated to stable organotin compounds. Pyrolysis then affords highly reactive fluoroacetylenes, e. g. 2.150... 

See other FLUORINATED ORGANOLITHIUM COMPOUNDS, HALO-ARYLMETALS... 

See other GRIGNARD reagents, halo-arylmetals, fluorinated organolithium COMPOUNDS... 

Heptafluoro-2-naphthyllithiuni prepared by metalation reaction can thermally decompose to a hexafluoro-l,2-naphlhalyne by elimination of lithium fluoride [36, 37] In this organolithium compound, fluorine elimination can occur from either position 1 or 3, however, no evidence for fluorine elimination from position 3 IS observed... 

The mechanism of the reaction between a hydrocarbon organolithium compound and a carbonyl compound is well-documented [69] and has been suggested earlier for fluorine-containing compounds [32, 68, 70] More recent studies on the mechanism have resulted m a better understanding ol this reaction [71] (equation 37)... 

Organolithium compounds can also react with fluorinated phosphorus derivatives. For example, aryl(difluoio)phosphanes 18 are formed by reaction of the corresponding aiyllithium compounds with phosphorus chloride difluoridc. The overall reaction is shown in Table I. This procedure has also been extended to the preparation of several cyclopentadienyl(di-fluoro)phosphane derivatives. ... 

B,B, 5"-Trichloroborazine is readily reduced with alkali metal hydroborates to yield borazine, (HBNH)3. The boron-bonded chlorine can be replaced by fluorine through the action of metal fluorides upon the trichloroborazine. With amines, the latter reacts to yield B,B, B"-triaminoborazines. The substitution of chlorine in iV-substituted B,B, B"-trichloro-borazines by organic groups is most easily achieved by the Grignard method but has also been effected by the use of organolithium compounds. 

Reaction with Organolithium Reagents. The fluorination of vinyl lithium derivatives with NFSi has been demonstrated in good yields with complete retention of configuration about the double bond. Phenyl lithium reacts rather poorly with 7V-fluorobenzenesulfonlmlde, but more complex phenyl lithium derivatives have been fluorinated to prepare fluoro- and polyfluoro-veratraldehydes as well as complex fluorinated polyaromatic compounds. Organolithium derivatives of heterocycles have been fluorinated by reaction with NFSi at low temperature. In this manner, fluoro-pyrroles and 2-fluoro-5-methylthleno[3,2-b]pyrldlne are prepared from their corresponding llthlo-parent compounds (eq 16). ... 

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