67705-05-9Relevant academic research and scientific papers
Gas-Phase Reaction between Oxygen (3P) Atoms and Hexafluoro-2-butyne
Mahaffy, Peter G.,Woude, Alex van der,Strausz, Otto P.
, p. 4289 - 4292 (1991)
The gas-phase addition of oxygen (3P) atoms from the mercury-sensitized photodecomposition of nitrous oxide to hexafluoro-2-butyne has been studied at 298 K.Tetrakis(trifluoromethyl)furan (4) is the major final product that arises from the reaction of the initial triplet ketocarbene adduct with a second molecule of hexafluoro-2-butyne.
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 (1994)
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.
Reactions involving fluoride ion. Part 41. Synthesis of hexakis(trifluoromethyl)cyclopentadiene and derived cyclopentadienide salts
Chambers, Richard D.,Gray, William K.,Vaughan, Julian F. S.,Korn, Stewart R.,Medebielle, Maurice,Batsanov, Andrei S.,Lehmann, Christian W.,Howard, Judith A. K.
, p. 135 - 145 (2007/10/03)
An efficient synthesis of hexakis(trifluoromethyl)cyclopentadiene 4, which shows a remarkably low reduction potential, is described. Various donors promote one-electron transfer to 4, leading to corresponding salts of pentakis(trifluoromethyl)cyclopentadienide 5. A novel approach to the synthesis of metal derivatives involves heating, or photolysis, of 4 directly with metals (including Cu, Ni, Fe and Co), leading to the corresponding ionic salts. X-Ray structural analysis was difficult because of rotation of trifluoromethyl groups in these salts, but structural data on 20, 24 and 30 has been obtained that reveals interesting conformations and stacking of the ions.
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 39. Reactions of Perfluorinated Dienes with Oxygen and Sulphur Nucleophiles
Briscoe, Mark W.,Chambers, Richard D.,Mullins, Steven J.,Nakamura, Takayuki,Vaughan, Julian F. S.
, p. 3119 - 3124 (2007/10/02)
The order of reactivity of perfluorinated dienes towards methanol is 3 > 2 >> 1 and the process is activated by release of angle strain.The diene 1 is hydrolysed to give perfluorotetramethyl-furan and the corresponding thiophene, is obtained by an analogo
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.
The Gas-Phase Photolysis of Perfluoro α-Diazo Ketones: Furan Formation and the Involvement of Transient Oxirenes
Mahaffy, P. G.,Visser, D.,Torres, M.,Bourdelande, J. L.,Strausz, O. P.
, p. 2680 - 2684 (2007/10/02)
The gas-phase photolyses of hexafluoro-3-diazo-2-butanone (1), octafluoro-2-diazo-3-pentanone (2), and octafluoro-3-diazo-2-pentanone (3) have been studied.Chemical trapping experiments with hexafluoro-2-butyne provide evidence that isomeric ketocarbene intermediates equilibrate, presumably via transient 4-?-electron oxirenes. 1 yields tetrakis(trifluoromethyl)furan (8) as a major product, with a trace of 1,2,3-tris(trifluoromethyl)-3-(trifluoroacetyl)cyclopropene (9) and bis(trifluoromethyl)ketene (10).Photolysis of either 2 or 3 yields the same four trapped products: 2-(pentafluoroethyl)-3,4,5-tris(trifluoromethyl)furan (12), 3-(pentafluoroethyl)-2,4,5-tris(trifluoromethyl)furan (14), 1,2,3-tris(trifluoromethyl)-3-(pentafluoropropionyl)cyclopropene (13), and 1,2-bis(trifluoromethyl)-3-(pentafluoroethyl)-3-(trifluoroacetyl)cyclopropene (15), in approximately the same ratio, along with the Wolff rearrangement product, (pentafluoroethyl)(trifluoromethyl)ketene (16).
