Fluoromethyl methyl carbonate

Nanbu, N. Watanabe, S. Takehara, M. Ue, M. Sasaki, Y., Electrolytic characteristics of fluoromethyl methyl carbonate for lithium rechargeable batteries, J. Electroanal. Chem. 2009, 625, 7-15. 

Among the carbonate solvents used in practical lithium batteries, linear carbonates such as dimethyl carbonate (DMC), ethyl methyl carbonate (EMC), and diethyl carbonate (DEC) are well-known good co-solvents (thinner) for EC and PC. The direct fluorination of DMC gave fluorinated derivatives such as mono-fluorinated one, fluo-romethyl methyl carbonate (FDMC), two di-fluorinated ones (bis(fluoromelhyl) carbonate, DFDMC, and difluormethyl methyl carbonate, gem-DFDMC), and tri-fluorinated ones (difluoromethyl fluoromethyl carbonate, TFDMC) as shown in Scheme 2.6 [33]. Three kinds of partially fluorinated DMCs except gm-DFDMC were obtained by fractional distillation of the fluorinated sample. 

Fluoromethyl phenyl sulfone, 135 Methylthiomethyllithium, 192 Methyl (trifluoromethylsulfonyl) methyl sulfone, 193 Addition a to selenium Potassium permanganate, 258 Other functionalized carbon reagents Allyltriphenylsilane, 13 Dicarbonyl(nitrosyl)-triphenylphosphinecobalt, 101... 

It is possible to halogenate selectively at the methyl position of alkylpyridines to give halogenoalkylpyridines. Low to moderate yields of fluoromethylpyridines are obtained on fluorination of 2- and 4-methyl pyridines with (V-fluoro-bis[(trifluoromethyl)sulfonyl]imide 52 in the presence of sodium carbonate in dichloromethane <1996T15>. 2-Methylpyridine is fluorinated in 20% yield and 4-methylpyridine in 72% yield under these conditions. Reagent 52 also effects the selective fluorination of 2,4,6-collidine to give the 2-fluoromethylated product in moderate yield (Equation 35). 

The a- and y -carbon atoms of methyl y-fluorobutjurate were fixed by making them part of a ring system. It was considered most unlikely that the animal body could degrade such compounds by a process of y -oxidation. The following compounds in this class were synthesized and found to be nontoxic methyl 2 fluoromethyl 4 5 dimetJiyl A tetrahydrobenzoate... 

Trifluoromethyl hypofluorite, CF3OF, is formed by the reaction of fluorine in excess with carbon monoxide, carbon dioxide, methanol, or other compounds containing both carbon and oxygen. In the procedure described below, carbon monoxide first reacts with an excess of fluorine to give largely carbonyl fluoride. The mixture is then passed through a hot tube where nearly all of the carbonyl fluoride reacts with fluorine to give trifluoromethyl hypofluorite. It is desirable to use somewhat more than two volumes of fluorine per volume of carbon monoxide. If this is not done, much perfluorodimethyl peroxide [bis(trifluoro-methyl) peroxide] is formed by the combination of carbonyl fluoride with tr fluoromethyl hypofluorite by the reaction ... 

The direct fluorination of PC and trans-butylcm carbonate (f-BC) gave four and two mono-fluorinated derivatives, respectively as shown in Scheme 2.4 [5, 26]. 4-Fluoromethyl-l,3-dioxolan-2-one (fluoromethylethylene carbonate, FMEC hereafter renamed as FPC for easy understanding), 4-fluoromethyl-5-methyl-l,3-dioxo-lan-2-one (fluormethylmethylethylene carbonate, FMMEC hereafter renamed as F- -BC for easy understanding) were obtained by fractional distillation of the fluorinated samples. 

Fig. 29. Sorption isotherms of carbon dioxide in (a) polycarbonate (PC), (b) silicone rubber, (o) tetramethylpolycarbonate (TMPC), and the fluorinated species wherein the methyls on the central carbon are fluoromethyl (CF3) groups, ie, hexafluoropolycarbonate (HFP(D) and tetramethylhexafluorocarbonate (TMHFPC). To convert MPa to psia, multiply by 145.

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