86236-55-7Relevant academic research and scientific papers
PRELIMINARY NOTE. Perfluorobicyclobutylidine: Unusual Reactivity Arising from Angle Strain
Chambers, Richard D.,Kirk, Julian R.,Taylor, Graham,Powell, Richard L.
, p. 393 - 396 (1983)
Perfluorobicyclobutylidine shows unusual reactivity in cycloaddition reactions in comparison with perfluoro-3,4-dimethylhex-3-ene.Reactions with 1,3-dienes are described giving 4? + 2? products; hydrogen transfer, and a copolymerisation have also been observed.
Reactions Involving Fluoride Ion. Part 31. Remarkable Reactivity of Perfluorobicyclobutylidene
Bayliff, Andrew E.,Bryce, Martin R.,Chambers, Richard D.,Kirk, Julian R.,Taylor, Graham
, p. 1191 - 1194 (2007/10/02)
Perfluorobicyclobutylidene (3) readily forms cycloadducts with butadiene, cyclopentadiene, 6,6-dimethylfulvene and furan, whereas perfluoro-3,4-dimethylhex-2-ene (2) is unreactive under the same conditions.This marked difference in reactivity between (2) and (3) is attributed to angle strain in (3).Reaction of the alkene (3) with cylohexa-1,3-diene yields 1H,1'H-perfluorobicyclobutyl (9) and benzene, by hydrogen transfer.The alkene (3) undergoes an 'ene' reaction with propene.Epoxides of perfluorobicyclobutylidene (3) and perfluorobicyclopentylidene (11) have been prepared; they both show high thermal stability and the latter epoxide fragments in the presence of fluoride ion to yield perfluorocyclopentene and perfluorocyclopentanone.
