Methyl fluoride formate

Ethyl fluoride shows more tendency to ionize in antimony pentafluoride, than does methyl fluoride. The solutions in neat antimony pentafluoride are, however, not stable and a rapid formation of t-butyl and t-hexyl cations is observed. This observation indicates self alkylation of ethylene formed in equilibrium of equation (2). 

CH3F methyl fluoride 593-53-3 3.220E+09 19.390 890 C2H402 methyl formate 107-31-3 5.090E+09 32.510... 

Appearance potentials for CHg from CH and CHgF reported by Losslng, Ingold, and Henderson ( ), the enthalpies of dissociation of hydrogen (104.20 kcal) and fluorine (37.72 kcal), and the enthalpy of formation of methane (-17.90 kcal) were used to calculate the enthalpy of formation of gaseous CHgF. These authors measured an appearance potential for CHg from CH F of 14.6 0.6 eV, which would give an uncertainty of about 15 kcal mol" in the enthalpy of formation of methyl fluoride. However, a correlation of the enthalpy of formation from the atoms of the methyl fluorides and methyl chlorides indicates that the uncertainty can be reduced to 7 kcal mol". ... 

CH3F) Predict the heats of formation for methyl fluoride and benzene by modeling... 

When CT4 is allowed to decay for several months in gaseous CH3F at 660 Torr, tritiated methyl fluoride is the only product detectable by radio GLC, with a 68% yield. Its formation has been traced to formation of a dimethylhalonium ion, follo>ving electrophilic attack to the n-center of the substrate (Equation 13) while the absence of labeled ethyl... 

No methylene chloride or chloroform was observed in the reaction. Under the used stable ion conditions, dimethylchloronium ion formation (equation 61) also occurs. This is, however, a reversible process and helps to minimize competing alkylation of methane to ethane (and higher homologs) which becomes more predominant when methyl fluoride is formed via halogen exchange. 

The formation of ethyl cyano(pentafluorophenyl)acetate illustrates the intermolecular nucleophilic displacement of fluoride ion from an aromatic ring by a stabilized carbanion. The reaction proceeds readily as a result of the activation imparted by the electron-withdrawing fluorine atoms. The selective hydrolysis of a cyano ester to a nitrile has been described. (Pentafluorophenyl)acetonitrile has also been prepared by cyanide displacement on (pentafluorophenyl)methyl halides. However, this direct displacement is always aecompanied by an undesirable side reaetion to yield 15-20% of 2,3-bis(pentafluoro-phenyl)propionitrile. 

Ab initio molecular orbital calculations are being used to study the reactions of anionic nucleophiles with carbonyl compounds in the gas phase. A rich variety of energy surfaces is found as shown here for reactions of hydroxide ion with methyl formate and formaldehyde, chloride ion with formyl and acetyl chloride, and fluoride ion with formyl fluoride. Extension of these investigations to determine the influence of solvation on the energy profiles is also underway the statistical mechanics approach is outlined and illustrated by results from Monte Carlo simulations for the addition of hydroxide ion to formaldehyde in water. 

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