- THE THERMAL CLEAVAGE OF BORON TRIS-TRIFLUOROMETHANESULFONATE (TRIFLATE) AND BORON TRIS-PENTAFLUOROETHANESULFONATE (PENTFLATE) TO TRIFLIC (PENTFLIC) ANHYDRIDE AND TRIFLUOROMETHYL TRIFLATE (PENTAFLUOROETHYL PENTFLATE)
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Cleavage of boron tris-trifluoromethanesulfonate(triflate) and boron tris-pentafluoroethanesulfonate(pentflate) was studied at 200 degC.Complete cleavage giving boron trifluoride, sulfur dioxide, carbonyl fluoride (trifluoroacetyl fluoride), triflic (pentflic) anhydride, triflic (pentflic) triflate (pentflate) and boric acid was observed.A mechanism for the cleavage based on formation of the identified compounds is suggested.
- Olah, G. A.,Weber, T.,Farooq, O.
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p. 235 - 242
(2007/10/02)
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- REACTIVITE DES ESTERS SULFONIQUES ET PYROSULFONIQUES PERFLUORES RFSO3RF ET RFSO3SO3RF. HETEROLYSE DE LA LIAION S-O
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Perfluoroalkyl perfluoroalkanesulfonates RFSO3R'F (RF, R'F = CF3, C2F5) and perfluoroalkyl perfluoroalkanepyrosulfonates RFSO3SO3RF, mixed with perfluoroalkanesulfonic acids (CF3SO3H or C2F5SO3H) decompose thermally.Depending on the starting materials, different products result from nucleophilic attack of a perfluoroalkanesulfonate anion of the acid on the sulfur atom of the sulfonate group of the ester, with heterolysis of the S-O bond.Therefore, under these conditions, the perfluorinated esters are not perfloroalkylating agents, but rather perfluorosulfonylating agents.
- Oudrhiri-Hassani, M.,Brunel, D.,Germain, A
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p. 163 - 178
(2007/10/02)
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- THERMOLYSE DES ANHYDRIDES PERFLUOROALCANESULFONIQUES. MECANISME ET APPLICATION A LA SYNTHESE DES ESTERS RFSO3RF.
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Perfluoroalkanesulfonic anhydrides FSO2)2O ; RF=CF3,C2F5,C4F9>, mixed with the parent acid, decompose thermally to give the corresponding perfluoroalkyl perfluoroalkanesulfonates (RFSO3RF) with liberation of SO2.If the perfluoroalkyl moieties in the anhydride and the acid are different, a mixture of symmetric and unsymmetric esters is obrained.An ionic bimolecular mechanism is deduced from the results, and a new easy synthesis of the symmetric perfluorinated sulfonic esters is proposed.
- Oudrhiri-Hassani, M.,Brunel, D.,Germain, A.,Commeyras, A.
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p. 219 - 232
(2007/10/02)
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- THERMAL STABILITY OF PERFLUOROALKANESULFONIC ACIDS AND THEIR ANHYDRIDES. NEW AND EASY APPROACH TO RFSO2ORF ESTERS.
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Perfluoroalkanesulfonic anhydrides (RFSO2)2O when mixed with acids decompose into perfluoroalkanesulfonic esters RFSO2ORF, thereby providing a new facile synthesis of these esters from perfluoroalkanesulfonic acids and phosphorus pentoxide.
- Hassani, M. Oudrhiri,Germain, A.,Brunel, D.,Commeyras, A.
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- OXYDATION ANODIQUE DE IODOPERFLUOROALCANES DANS LES ACIDES PERFLUOROALCANESULFONIQUES. PREPARATION DE NOUVEAUX ESTERS SULFONIQUES TOTALEMENT FLUORES RFSO3R'F A LONGUES CHAINES
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Perfluorinated sulphonic esters RFSO3R'F and fluorosulphates FSO3R'F, are easily obtained by anodic oxidation of iodoperfluoroalkanes R'FI in perfluoroalkene sulphonic acids RFSO3H (RF=CF3, C2F5, C4F9) and fluorosulphuric acid.With di-iodo compound I(CF2)4I, the mono and the diester can be selectively obtained.The alkaline hydrolysis of these esters produces perfluorinated carboxylic compounds.Polyfluorinated iodide R'FCH2CH2I are also oxidized in similar conditions.The mechanism of the electrolytic reaction is discussed.
- Germain, A.,Commeyras, A.
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p. 487 - 492
(2007/10/02)
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