31462-65-4Relevant academic research and scientific papers
POLYFLUOROBICYCLOOCTANES. PART III. SYNTHESES AND REACTIONS OF NEW MONO- DI- AND TRIHYDRIDES AND DERIVED COMPOUNDS
Battersby, J.,Stephens, R.,Tatlow, J. C.,Thomas, L. F.
, p. 139 - 162 (1980)
Fluorobicyclooctanes as follows were made by fluorination with cobaltic fluoride: 1H- and 2H-tridecafluoro-; 1H,2H-, 1H,3H-, 2H,2H-, 2H,3H, and 1H,4H-dodecafluoro-; 1H,2H,3H-, 1H,2H,4H-, and 1H,3H,3H-undecafluoro-; 2H,2H,3H,3H-decafluoro-.These afforded, by the appropriate dehydrofluorinations, dodecafluoro-; 1H- and 2H-undecafluoro; 1H,2H-, 1H,3H-, and 1H,4H-decafluoro-bicyclooct-2-ene.Self-consistent nmr data confirmed all structures. 1H-Trideca- and 1H,4H-dodeca-fluorobicyclooctanes possess acidic bridgehead hydrogens, which are reactive under basic conditions, and may be replaced by various functional groups. 1-Lithiotridecafluorobicyclooctane, a remarkably stable perfluoroalkyl lithium derivative, survived many hours in refluxing ether, but slowly decomposed to 1-substituted undecafluorobicyclooct-2-enes, via a transient intermediate, a bridgehead 'olefin' 'violating' Bredt's rule.
