Abstract: A method of making TFPX using an SN2 type nucleophilic displacement reaction. The method includes reacting a nucleophilic fluorine molecule with a nonfluorinated-tetrahalo-p-xylene molecule. Exemplary nucleophilic fluorine molecules include, but are not limited to, CsF, KF, NaF and LiF. The nonfluorinated-tetrahalo-p-xylene molecules may include, &agr;,&agr;,&agr;′,&agr;′-tetrachloro-p-xylene, &agr;,&agr;,&agr;′,&agr;′-tetrabromo-p-xylene or &agr;,&agr;,&agr;′,&agr;′-tetraiodo-p-xylene. The reaction may be carried out in an open or closed container. Furthermore, the reaction may be carried out in the presence of a phase transfer catalyst. In certain embodiments, the reaction is carried in a substantially solvent-free environment.

Abstract: A process for the preparation of octafluoro-?2,2!paracyclophane includes contacting a reactant selected from the group consisting of 1,4-bis(bromodifluoromethyl)benzene (dibromide), 1,4-bis(chlorodifluoromethyl)benzene (dichloride), and 1,4-bis(iododifluoromethyl)benzene (diiodide) with trimethylsilyltributyltin (TMSTBT) (a reducing agent) and fluoride ions in a refluxing solution of hexamethylphosphoramide (HMPA) or dimethylsulfoxide (DMSO) in tetrahydrofuran (THF) at conditions effective to promote a reaction product comprising octafluoro-?2,2!paracyclophane.

Abstract: A process for the preparation of octafluoro-[2,2]paracyclophane includes contacting a reactant selected from the group consisting of 1,4-bis (bromodifluoromethyl)benzene (dibromide), 1,4-bis (chlorodifluoromethyl)benzene (dichloride), and 1,4-bis (iododifluoromethyl)benzene (diiodide) with trimethylsilyltributyltin (TMSTBT) (a reducing agent) and fluoride ions in a refluxing solution of hexamethylphosphoramide (HMPA) or dimethylsulfoxide (DMSO) in tetrahydrofuran (THF) at conditions effective to promote a reaction product comprising octafluoro-[2,2]paracyclophane.