Multiple electrophilic substitution of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Synthetic methods for introduction of two substituents into the rings of oc tafluoroparacyclophane are presented. Nitration gives three isomers with ni tro substituents on different rings: pseudoortho, pseudo-mete, and pseudo-p ara, in equal amounts. These dinitro compounds are shown to be precursors o f a variety of other disubstituted OFF derivatives. Methods of characteriza tion of isomeric disubstituted OFPs are extensively discussed, and the H-1 and F-19 NMR spectra of these derivatives are analyzed explicitly.