374-79-8

Upstream product

• 374-65-2 1-Trifluormethyl:4H/-decafluor-cyclohexan 
• 31665-17-5 1-Trifluoromethylheptafluorocyclohexa-1,4-diene 
• 14100-80-2 trans 4H-1-trifluoromethyldecafluorocyclohexane 
• 14100-81-3 cis 4H-1-trifluoromethyl/-decafluorocyclohexane 

Relevant academic research and scientific papers

FLUORINATION OF POLYHALOGENATED UNSATURATED COMPOUNDS WITH VANADIUM PENTAFLUORIDE

Vanadium pentafluoride reacts with polyfluorinated and polychlorinated olefins, alkadienes, cycloalkenes and cyclodienes in CFCl3 or without a solvent at -25 deg C to 100 deg C, forming products of addition of two fluorine atoms across the C=C bond.

POLYFLUOROCYCLOALKENES. PART XIX. SOME REACTIONS AND COMPOUNDS FROM 1,2-BIS(TRIFLUOROMETHYL)OCTAFLUOROCYCLOHEXENE

The title compound (A) gave a dichloro-adduct (D), which with lithium aluminum hydride yielded a complex mixture, from which a trace of trans 1H,2H-1,2-bis(trifluoromethyl)octafluorocyclohexane (E) was isolated.Catalytic hydrogenation of olefin (A) afforded cis 1H,2H-1,2-bis(trifluoromethyl)octafluorocyclohexane (C), and a small amount of 6H-1,6-bis(trifluoromethyl)heptafluorocyclohexene (B).Dehydrofluorination of the cis dihydride (C) by aqueous potash gave olefin (B) and 2,3-bis(trifluoromethyl)hexafluorocyclohexa-1,3-diene (G): fluorination of (G) by cobalt(III) fluoride gave back (A).Fluorination of compounds (C) and (B) afforded cis and trans 1H-1,2-bis(trifluoromethyl)nonafluorocyclohexane (J and H respectively).Both (H) and (J) were dehydrofluorinated to give olefin (A) exclusively, i.e. fluorine was lost preferentially from the tertiary ->C-F group.Ammonia and (A) gave 1,3-diamino-2-cyano-3-trifluoromethylhexafluorocyclohexene (K).Some hydro-polyfluoro-cyclohexanes took up small proportions of deuterium during dehydrofluorinations in the presence of deuterium oxide,but no interconversions of pairs of stereoisomers were observed.

FLUOROCYCLOHEXANES. PART XVI. THE SIX H-TRIFLUOROMETHYLDECAFLUORO- AND TWO OF THE 2H,4H-TRIFLUOROMETHYLNONAFLUORO-CYCLOHEXANES

Fluorination of benzotrifluoride by cobaltic fluoride at 260-280 deg gave, besides the fluorocarbon, the six possible tridecafluoromethylcyclohexane isomers, and two 2H,4H-dodecafluorides.Of the C7HF13 compounds, only the cis-2H-, and the cis- and trans-4H-isomers could be isolated pure.The two 3H-isomers were made by pyrolysis of perfluoro(1-methyl-3-isopropylcyclohexane) in the presence of toluene.The trans-2H-isomer was made by further fluorination of one of the 2H,4H-dodecafluorides.Aqueous potash and the cis-2H-tridecafluoride gave 1-trifluoromethylnonafluorocyclohex-1-ene, which with stronger alkali hydrolysed to 1-carboxynonafluorocyclohex-1-ene.The cis- and trans- 2H and 4H-tridecafluorides were dehydrofluorinated by sodium fluoride at 320-380 deg (the cis-isomer of each pair reacted faster than the trans-: axial versus equatorial hydrogen) to give, respectively, the 1-trifluoromethylnonafluoro-ene and the 4-trifluoromethyl-isomer.The latter was isomerised to the former by sodium fluoride at 500-600 deg.The 1-CF3-ene gave hexafluoroglutaric acid on oxidation with alkaline potassium permanganate.