22060-77-1Relevant articles and documents
The synthesis of I·-1,2,3,4,5,6-hexafluorocyclohexane (benzene hexafluoride) from benzene
Durie, Alastair J.,Slawin, Alexandra M. Z.,Lebl, Tomas,O'Hagan, David
, (2012)
Six of the best: Benzene had been used by Faraday and Mitscherlich in their respective synthesis of hexachloro- and hexabromocyclohexane in the early 19th century. Also starting from benzene, I·-1,2,3,4,5,6- hexafluorocyclohexane (benzene hexafluoride; se
Trifluoromethanesulfonic acid: A novel solvent for the electrophilic fluorination of fluoroaromatics
Coe, Paul L.,Stuart, Alison M.,Moody, David J.
, p. 1807 - 1811 (2007/10/03)
Trifluoromethanesulfonic acid has been discovered to be an excellent new solvent for promoting the direct elemental fluorination of aromatics. Fluorobenzene has been successfully fluorinated to a mixture of 1,4-difluorobenzene (31%) and 1,2-difluorobenzene (7%) in CFCl3-CF3SO3H (5%), but no further improvement is observed by the addition of boron trifluoride. When the reaction is carried out in only CFCl3, the main reaction pathway is the 1,2- and 1,4-addition of fluorine to fluorobenzene forming cyclohexenes of molecular formula C6H5F5, and only a small amount of 1,4-difluorobenzene is produced. Although both 1,2- and 1,3-difluorobenzene are fluorinated to 1,2,4-trifluorobenzene in CFCl3-CF3SO3H (10%), 1,4-difluorobenzene does not undergo the same electrophilic substitution reaction.
Oxidative fluorination in amine-HF mixtures
Meurs,Eilenberg
, p. 705 - 714 (2007/10/02)
The selective electrochemical fluorination of alkenes, phenanthroline, naphthalene and chlorobenzene in neat amine-HF mixtures is described, together with the chemistry of 4,4-difluorocyclohexadienone.
New Method for Selective Monofluorination of Aromatics Using Silver Difluoride
Zweig, Arnold,Fischer, Robert G.,Lancaster, John E.
, p. 3597 - 3603 (2007/10/02)
Fluorobenzene is obtained in 61percent yield from reaction of a solution of benzene in n-hexane with solid argentic fluoride (AgF2).The AgF2 acts as both a strong oxidant and the fluoride source.Cobaltic fluoride provides only low (8percent) yields of fluorobenzene under similar conditions.The predominant reaction of benzene solutions with AgF2 appears to proceed by a process involving initial electrophilic oxidative cis addition of two fluorine atoms from the solid AgF2 lattice to the para aromatic positions, leading to cis-3,6-difluoro-1,4-cyclohexadiene (F2CHD).The reductive elimination leaves solid argentous fluoride (AgF) which is easily recoverable by filtration.Elimination of HF from the F2CHD yields fluorobenzene.Reactions of haloaromatics with AgF2 generally proceed in a similar manner.Thus, further reaction of AgF2 with benzene or monohalo- or p-dihalobenzenes leads in steps to 3,3,6,6-tetrafluoro-1,4-cyclohexadiene (F4CHD) in up to 82percent yield.The modest to high yields of mono- and specific polyfluorinated aromatics contrast sharply with reported nonselective perfluorination in vapor-phase reactions of aromatics over AgF2 or CoF3.Reactions of AgF2 or CoF3 with solutions of nitrobenzene, acetophenone, benzoic acid, and benzonitrile give mixtures of o-, m-, and p-monofluoro derivatives.
