Chlorotrifluoroethylene, reaction with

Chlorotrifluoroethylene, reaction with aqueous sodium cyanide to form 3-chloro-2,2,3-trifluoropropionic acid, 11... 

Preference for reaction with the unlike monomer occurs when ri is less than 1. When r and T2 are approximately equal to 1, the conditions are said to be ideal, with a random (not alternating) copolymer produced, in accordance with the Wall equation. Thus, a random copolymer (ideal copolymer) would be produced when chlorotrifluoroethylene is copolymerized with tetrafluoroethylene (Table 7.1). 

The data for competition between formation of (19) and (20) in aliphatic systems are more limited, but they are only partly accounted for by the carbanionic theory. Attack on chlorotrifluoroethylene, for example, is nucleophile-dependent fluorine from the CF2 group is replaced on reaction with PhMgBr (Tarrant and Warner, 1954), PhLi (Dixon, 1956) and LiNBu2 (Yakubovich et al., 1966), while Re(CO) ... 

HF reaction with 3-chloro-pentafluoro-l-propene (CF2=CF-CF2C1) at 200°C, catalyzed by activated carbon, yields HFP. l Hexafluoropropylene can be prepared from the catalytic degradation of fluoroform (CHF3) at 800-1000°C in a platinum-lined nickel re-actor.l l Another method is copyrolysis of fluoroform and chlorotrifluoroethylene (CF2=CFCl),f l or chlorodifluoromethane and l-chloro-1,2,2,2-tetrafluoroethane (CHClFCFg), giving good yields of HFP. 

Product distributions from the disproportionation of l,l,2,3-tetrachloro-3, 3-difluoropropene (2CFsCFCCl CClj- CFj Ca Cai+CFa,CCI CCIg 2CFCljCCl CCl4- CF,ClCa CCl, + CCl,Ca Ca,) at 50 C with aluminium halides, titanium tetrachloride, and antimony pentachloride have been determined. Formation of the bromo-olefin CF,-CCl CBrCl in the reaction with aluminium bromide was rationalized in trams of the HSAB concept, and related known reactions were interpreted similarly. Replacement of vinylic fluorine by iodine has been shown to occur udien tetrafluoro-ethylene or chlorotrifluoroethylene is treated with methyl iodide and aluminium chloride. ... 

The complex [(acac)Rh(PhjPMe)2] reacts with tetrafluoroethylene and chlorotrifluoroethylene to yield the rhodacyclopentane complexes (131), but with bromotrifluoroethylene, complex (132) is formed. In the reaction with 1,2-dichlorotetrafluorocyclobutene, transfer of chlorine to metal occurs, giving the vinylic complex (133). The complex [(acac)Rh(Ph2PMe)j] reacts with only one mole of hexafluoroacetone, yielding (134), but with the corre-... 

Chloro-2,2,3-trifluoropropionic acid has been prepared by permanganate oxidation of 3-chloro-2,2,3-trifluoropropanol which is one of the telomerization products of chlorotrifluoroethylene with methanol. The present procedure is a modification of one reported earlier and is undoubtedly the method of choice for making propionic acids containing 2 fluorine atoms, i.e., 2,2,3,3-tetrafluoropropionic acid, 3,3-dichloro-2,2-difluoropropionic acid, and 3-bromo-2,2,3-trifluoropropionic acid. When preparing 2,2,3,3-tetrafluoropropionic acid from tetrafluoroethylene, it is desirable to use an additional 50 ml. of acetonitrile and externally applied heat to initiate the reaction. 

A -Halogenated compounds such as iV-chlorotnfluoroacetamide, A -chloro-imidosulfuryl fluonde and N N dichlorotnfluoromethylamine add across C=C bonds to form saturated amides [14] tmidosulfury I fluorides [15] and amines [16], respectively Allylic halogenation also occurs with the use of A-bromo- or A-chIo roperfluoroamides The primary amine A,A-dichlorotrifluororaethylamine selectively affords 11 or 2 1 adducts with either tetrafluoroethylene or chlorotrifluoroethylene [16] (equation 7) The reaction mechanism is believed to involve thermal free radicals, with control achieved principally by reaction temperature The 1 1 adduct is formed even in the presence of a large excess of olefin... 

Perfluoroisobutylene undergoes cycloadditions with azides only at elevated temperatures, the reaction can lead to subsequent loss of nitrogen [6] (equation 4) In another high-temperature reaction, chlorotrifluoroethylene undergoes cy cloaddition with the azomethineylide generated from the thermal electrocyclic nng opening of an azindine, a reaction that contributes to a good overall synthesis of 3,4-difluoropyrroles [7] (equation 5)... 

The synthesis of 2-chloro-2,3,3-trifluorocyclobutyl acetate illustrates a general method of preparing cyclobutanes by heating chlorotrifluoroethylene, tetrafluoroethylene, and other highly fluorinated ethylenes with alkenes. The reaction has recently been reviewed.11 Chlorotrifluoroethylene has been shown to form cyclobutanes in this way with acrylonitrile,6 vinylidene chloride,3 phenylacetylene,7 and methyl propiolate.3 A far greater number of cyclobutanes have been prepared from tetrafluoroethylene and alkenes 4,11 when tetrafluoroethylene is used, care must be exercised because of the danger of explosion. The fluorinated cyclobutanes can be converted to a variety of cyclobutanes, cyclobutenes, and butadienes. 

The photoinitiated reaction of 1,2-dibromo-l-chlorotrifluoroethane with chlorotrifluoroethylene gives the first two telomers (ref. 28). 

With chlorotrifluoroethylene the following peroxidation reaction was iderrtified ... 

Many vinyl monomers were reported to have been grafted onto fluoropolymers, such as (meth)acrylic acid and (meth)acrylates, acrylamide, acrylonitryl, styrene, 4-vinyl pyridine, N-vinyl pyrrolidone, and vinyl acetate. Many fluoropolymers have been used as supports, such as PTFE, copolymers of TFE with HFP, PFAVE, VDF and ethylene, PCTFE, PVDF, polyvinyl fluoride, copolymers ofVDF with HFP, vinyl fluoride and chlorotrifluoroethylene (CTFE). The source of irradiation has been primarily y-rays and electron beams. The grafting can be carried out under either direct irradiation or through the use of preliminary irradiated fluoropolymers. Ordinary radical inhibitors can be added to the reaction mixture to avoid homopolymerization of functional monomers. 

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