Multiple electrophilic substitution of 1,1,2,2,9,9,10,10-octafluoro
Synthetic methods for introduction of two substituents into the rings of octafluoroparacyclophane are presented. Nitration gives three isomers with nitro substituents on different rings: pseudo-ortho, pseudo-meta, and pseudo-para, in equal amounts. These dinitro compounds are shown to be precursors of a variety of other disubstituted OFP derivatives. Methods of characterization of isomeric disubstituted OFPs are extensively discussed, and the 1H and 19F NMR spectra of these derivatives are analyzed explicitly.
Roche
AJ
Department of Chemistry, University of Florida, Gainesville 32611-7200, USA.
Dolbier
WR