10575-61-8Relevant academic research and scientific papers
Reactions involving fluoride ion. Part 47: Reactions of perfluorobicycloalkenes
Chambers, Richard D.,Nakamura, Takayuki
, p. 398 - 406 (2007/10/03)
Electron deficient dienes 3 and 4 are obtained by defluorination of perfluorobicyclo-butylidene (1) and -pentylidene (2), using tetrakis(dimethylamino)ethene (TDAE), and these dienes are very reactive. With alkali metal fluorides, 4 gave a stable observable anion while 3 gave oligomers. The corresponding fluorinated allyl anion was however obtained via 3 in the presence of TDAE. Further reactions of 3 and 4 are described.
Charge-transfer salts containing cyclic perfluorinated anions
Briscoe, Mark W.,Chambers, Richard D.,Clegg, William,Gibson, Vernon C.,Mullins, Steven J.,Vaughan, Julian F.S.
, p. 1 - 2 (2007/10/03)
Perfluorobicyclopentenyl (1a) and -butenyl (2a) react with decamethylferrocene (3), to give charge-transfer salts 4 and 5, respectively; perfluorohexakis (trifluoromethyl) cyclo-pentadiene (6) forms a salt (8) containing the C5(CF3)5 anion. Crystal structures of the salts 4 and 5 have been determined; both contain centrosymmetric trans-diene radical anions.
Fluorinated di-enes
Chambers, R. D.,Vaughan, J. F. S.,Mullins, S. J.,Nakamura, T.,Roche, A. J.
, p. 231 - 234 (2007/10/02)
Fluorinated di-enes may be obtained by the defluorination of some oligomers of F-alkenes and -cycloalkenes using tetrakis(dimethylamino)ethene.These di-enes are very susceptible to nucleophilic attack.Nucleophilic epoxidation of (4) gives a new diepoxide which undergoes a novel ring-opening reaction.Di-ene (4) forms cyclopentadienylide derivatives with di-functional carbon nucleophiles and a cyclopentadienylide salt (17) is obtained in a remarkable 'one-pot' reaction from hexachlorobutadiene. (4) (17) - Keywords: Fluorinated di-enes; Tetrakis(dimethylamino)ethene; Defluorination
Reactions Involving Fluoride Ion. Part 38. New Fluorinated Dienes by Defluorination
Briscoe, Mark W.,Chambers, Richard D.,Mullins, Steven J.,Nakamura, Takayuki,Vaughan, Julian F. S.,Drakesmith, Frederick G.
, p. 3115 - 3118 (2007/10/02)
The oligomers 2, 4 and 6, 6a, derived from tetrafluoroethene, octafluorocyclopentene, and hexafluorocyclobutene respectively, are converted into their corresponding dienes 7-9 by defluorination, using sodium amalgam.An alternative route using tetrakis(dimethylamino)ethene (TDAE) is also described and forms a fluoride salt of TDAE.The diene 7 shows a remarkably low extinction coefficient for UV absorption.
A Synthesis of Novel Perfluorodienes
Briscoe, Mark W.,Chambers, Richard D.,Mullins, Steven J.,Nakamura, Takayuki,Drakesmith, Frederick G.
, p. 1127 - 1128 (2007/10/02)
Oligomers of perfluoroalkenes are converted to dienes in good yields, using sodium amalgam; these dienes are highly susceptible to nucleophilic attack and can be excellent sources of heterocycles.
