A New Synthesis of Octafluoroparacyclophane

Article abstract of DOI:10.1021/jo00059a038

A new synthesis of 1,1,2,2,9,9,10,10-octafluoro<2.2>paracyclophane (2) is reported.Easy preparation of gram quantities of 2 is accomplished by treatment of α,α'-dibromo-α,α,α',α'-tetrafluoroxylene with a complex low-valent form of Ti which is made by reduction of TiCl4 with equimolar quantities of LiAlH4 in THF.Use of high-dilution techniques is required for the reaction to be successful.The formation of 2 is believed to proceed via the reactive monomeric species α,α,α',α'-tetrafluoro-p-xylylene (4).