J. Tatlow
Nov 1, 1995
Citations
0
Influential Citations
10
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Work by the Fluorine Research Group at the University of Birmingham is reviewed. Families of polyfluoro-cyclo-hexanes, -butanes, -pentanes and -heptanes, and of -oxolans, -thiolans, - N -methylpyrrolidines and -2-methyloxolans were made. From them, eliminations of hydrogen fluoride gave derived cyclo-enes and -dienes. Precise stereochemical structures were allocated to all of the compounds. Highly fluorinated bicyclo-[2,2,1] heptanes and -[2,2,2] octanes were also made, including some with a bridgehead position bearing hydrogen. The acidities of these had repercussions on theories of negative hyperconjugation. Further, they underwent direct exchange, readily affording organometallic derivatives which were versatile synthetic intermediates via replacement of the metal. Also, however, by eliminations of metal fluoride they gave the first observed examples of highly strained ‘bridgehead olefins’.