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 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...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-08, Vol.65 (17), p.5282-5290
Main Authors: Roche, Alex J, Dolbier, William R
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000436x