Nucleophilic Reactions of Fluoroölefins

England, David C.; Melby, L. R.; Dietrich, Manfred; Lindsey, R. V.

doi:10.1021/ja01504a026

Cited by 86 publications

(39 citation statements)

References 0 publications

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“…Fluoroalkyl alkyl or fluoroalkyl aryl ethers are prepared from alkoxides or phenoxides and fluoroolefins [215]; for example, 1,1,2,2-tetrafluoro-1-methoxyethane [425-88-7] is prepared from tetrafluoroethylene and sodium methoxide-methanol. Higher perfluoroolefins can also be employed [216].…”

Section: Partially Fluorinated Ethersmentioning

confidence: 99%

Fluorine Compounds, Organic

Siegemund

Schwertfeger

Feiring

et al. 2016

Ullmann's Encyclopedia of Industrial Chemistry

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Section: Partially Fluorinated Ethersmentioning

confidence: 99%

Fluorine Compounds, Organic

Siegemund

Schwertfeger

Feiring

et al. 2016

Ullmann's Encyclopedia of Industrial Chemistry

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“…The reaction of five-membered aromatic heterocycles with tetrafluoroethylene and chlorotrifluoroethylene produced early examples of such compounds, including N-tetrafluoroethylpyrrole formed by the reaction of the potassium salt of pyrrole with tetrafluoroethylene. 175 Recently, Yagupolskii and coworkers have undertaken an extensive investigation of nitrogen-containing heterocycles possessing perfluorinated alkyl groups directly attached to nitrogen. [176][177][178][179] Potassium salts of a set of heterocycles with different basicities, including imidazole, 2-methylebenzimidazle, 3,5-dimethylpyrazole, 1,2,4-triazole, and benzotriazole, were chosen for reactions with tetrafluoroethylene, chlorotrifluoroethylene, and 1,2-dichlorodifluoroethylene ( Fig.…”

Section: N-perfluoroalkylated Nitrogen Heterocyclesmentioning

confidence: 99%

Fluorinated Five‐Membered Nitrogen‐Containing Heterocycles

Kirk¹

2009

Fluorinated Heterocyclic Compounds

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“…As me ntio ned before, it had bee n fo und diffic ult to e ffec t the successful cleavage of the e thoxy e ther of he ptaAu oro-p-cresol by c he mical means [141 Howe ve r , the relative in s ta bility of other t-butyl e the rs to both heat a nd acid [16][17][18] s uggested that the tbutyl e ther of hepta flu oro-p -cresol might poss ibl y undergo fac ile clea vage to th e desired c resol. Ind eed , it was fo und th a t by eith er liquid ph ase or vapor pyrol ys is the e ther undergoes clea vage to give heptaflu oro-pcresol a nd iso but ylene.…”

Section: Synthesis Of 2356-tetrafluoro-4-trifluoromethylphenol (Hementioning

confidence: 99%

Synthesis of poly-p-oxyperfluorobenzylene and related polymers. A novel synthesis of the monomer 2,3,5,6-tetrafluoro-4-trifluoromethylphenol

Antonucci¹,

Wall²

1967

J. RES. NATL. BUR. STAN. SECT. A.

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The sy nth esis and polymerization of 2,3,5,6-tetraAuoro-4-triA uoromethylphenol (he ptaAuoro-pcres ol) is desc ribed. Th e polymer , po ly-p-oxype rAu orobenzyle ne (polyperAuoro-p-benzy le ne oxide), is probab ly formed thro ugh the perAuoro -p-quinon e me th id e inte rm e di ate obtaine d by the intramol ec ular loss of e ithe r hydroge n Au oride or a me tal Au orid e. Th e polymer has a s tru c ture a nal ogo us to th at reported for the polymer d erive d from p-triAuoro me thy lphe no l und e r s imil ar co nditi ons.[n th e co urse of th e syn th es is of th e monom er, he ptafluoro-p-c reso l, a novel s yntheti c me thod was dis co vered. Th e sy nthes is cons ists in the prior preparation of I -t-but oxy-2,3,5,6-tetrafluoro -4-triAu orom e thylbenze ne and its s ubsequ e nt th ermal d eco mposition into th e isobutyl ene and the des ire d cresol. S imil arly, N-t-butyl-2,3,5,6-tet raAuoro-4-triAu orome th ylaniline und ergoes a s imil ar liquid phase pyrolys is into isobutyle ne and 2,3,5,6-tetraAuoro-4-triAu oromet hylaniline. However, during the course of thi s pyrolys is, prac ti ca ll y a ll of the ani line undergoes po lymerization with the concomitant los s of hydrogen Au orid e. T he polymer is form e d by th e same mec hani s m operative in the thermal po lymerization of p-heptafluorocresol exce pt th a t additional quantiti es of hydrogen Auoride ca n be elimin ated from th e -NHCF, -segme nts of the polymer c hain the re by introd uc ing -N = CF -units into the polymer bac kbone .Other t-b utyl derivatives were sy nthes ized and th e ir thermal deco mposition studied. Several poss ibl e mec hani s ms for the deco mpos ition of these t-butyl co mpo und s a re considered _ Key Words: I -t-Butoxy-2,3,5,6-te traAu oro-4-triAuorom e th ylbe nzen e , perAuoro-p-quinon e met hid e, po lyme rization, poly-p-oxyperAuorobenzy le ne, pyrolysis, 2,3,5,6-tetrafluoro-4-triAu orome thylph enol.

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Nucleophilic Reactions of Fluoroölefins

Cited by 86 publications

References 0 publications

Fluorine Compounds, Organic

Fluorine Compounds, Organic

Fluorinated Five‐Membered Nitrogen‐Containing Heterocycles

Synthesis of poly-p-oxyperfluorobenzylene and related polymers. A novel synthesis of the monomer 2,3,5,6-tetrafluoro-4-trifluoromethylphenol

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