Chlorine monofluoride, addition reaction

The effect of the substituent group can be seen in the reactions of the following senes of halogenated esters Methyl 2,3 dichloro-3-fluoro-2-methylpropionate and chlorine monofluoride first form methyl 2-chloro-3,3-difluoro-2-methylpro-pionate An additional equivalent of chlorine monofluoride produces methyl 2 methyl-2,3,3-trifluoropropionate (equation 14)... 

The reaction of perfluorovinylamines with chlorine monofluoride results in bidirectional addition to form a mixture of isomers, e.g. 1 and 2 (1/2 = 69 31) in 95% yield.25... 

The stoichiometric equivalents of halogen fluorides, i.e. chlorine monofluoride, bromine monofluoride and iodine monofluoride, have found a wide application in addition reactions to double bonds. The equivalents are obtained by reacting A -haloamides or free halogens in combination with hydrogen fluoride or its salts as the source of fluoride ions. The reactions proceed under mild conditions at — 80 to 20 "C in anhydrous hydrofluoric acid or diethyl ether, tetrahydro-furan, dichloromethane or chloroform mainly by electrophilic addition with Markovnikov-type regioselectivity (anti addition).26-28... 

Boron trifluoride and boron trifluoride-diethyl ether complex can be used as a source of fluoride ions in the presence of hypobromites and hypochlorites, e.g. methyl hypobromitc, tert-butyl hypobromite, methyl hypochlorite in carbon tetrachloride at 25 C. The addition of bromine monofluoride" and chlorine monofluoride" to various alkenes is accompanied by the formation of the corresponding alkoxybromides and alkoxychlorides which hinder the isolation of the halofluorinated products.57 jV-Bromo- and A -chloro-substiluted alkyl- and arylamines. -amides, and -imides, A -chloro-A,-methylamine, A -bromo-A -methylamine, A -chloro-A, /V-dimethylamine, A-bromo-A.A-dimethylamine, ACV-dichloro-A -methylamine, V,fV-dibromo-,V-mcthylaminc, A -bromosuccinimide, -V-chlorosuccinimide, Af-bromoacct-amide, A.A -dichlorourethane, can be used in the reaction instead of the hypohalites. The reactions with various alkenes conducted in dichloromethane at room temperature in the presence of boron trifluoride-diethyl ether complex produce bromofluoro and chlorofluoro addition products in 40-80 % yield. However, the reactions are complicated by the addition of A -halo-succinimides and Af.A-dichlorourcthane to the C = C bonds.58... 

Chlorine monofluoride is capable of oxidizing a sulfur atom bonded to one or two perfluoroalkyl groups through the addition of two or four fluorine atoms to the sulfur atom, depending on the ratio of the reagents and the reaction temperature. 

Chlorine monofluoride (which is commercially available) acts as a powerful fluorinating and oxidizing agent (e.g. reaction 16.19) oxidative addition to SF4 was shown in Figure... 

Chlorine monofluoride (which is commercially available) acts as a powerful fluorinating and oxidizing agent (e.g. reaction 17.22) oxidative addition to SF4 was shown in Figure 16.13. It may behave as a fluoride donor (equation 17.23) or as a fluoride acceptor (equation 17.24). The structures of [C12F] (17.9) and [C1F2] (17.10) can be rationalized using the VSEPR model. Iodine monochloride and monobromide are less reactive than CIF, but of importance is the fact that, in polar solvents, ICl is a source of I" " and iodinates aromatic compounds. 

Nitrosyl fluoride also catalyses the addition of chlorine monofluoride (and of fluorine) across G=0 bonds in fluorocarbonyl compounds, the reaction apparently proceeding via initial formation of a-fluoro-nitrites. Apparently, no reaction occurs between carbon dioxide and chlorine monofiuoride in the presence of caesium fluoride in the temperature range -78 to 80 G [c/. CO3 + 2F °S GF COF), (100%)], but thionyl... 

Trifluoromethylsulphur chloride tetrafluoride, CF3-SF4C1 (which possesses a tronj-octahedral configuration so that all four fluorines attached to sulphur are equivalent), has been prepared by reaction of trifluoromethylsulphur trifluoride with chlorine in the presence of caesium fluoride at room temperature this synthesis is analogous to that of sulphur chloride pentafluoride from sulphur tetrafluoride, chlorine, and caesium fluoride, a method claimed to be inferior to the addition of chlorine monofluoride to sulphur tetrafluoride in the presence of caesium fluoride specially activated by a fusion-solidification-fine-grinding technique. Bis(perfluoroalkyl)-sulphur difluorides result from the fluorination of bis(perfluoroalkyl) sulphides with chlorine monofluoride ... 

Graphite may be the thermodynamically most stable modification of carbon. StUl it is chemically attacked more easily than diamond due to its layered structure and the comparatively weak interaction between the graphene sheets. Altogether the graphite s reactivity toward many chemicals is rather low nevertheless. With chlorine, for example, it does not react at all under usual conditions, and even with fluorine reaction occurs only at more than -400 °C. Suitable performance yields the transparent, colorless carbon monofluoride CF (up to CF1.12 due to additional fluorine atoms at marginal positions and defects), a chemically very resistant... 

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