Tetrabutylphosphonium fluoride

Tetrabutylphosphonium fluoride, tetrabutylphosphonium hydrogen difluoride and tetrabutylphosphonium dihydrogen trifluonde can be prepared from tetrabutylphosphonium hydroxide and hydrogen fluoride (equation 19)... 

Reeently, new fluorinating agents, tetrabutylphosphonium fluoride and its mono- and dihydrofluoride, were used for preparation of fluorohydrins from epoxides [14] (equation 13). 

Recently, silicon tetrafluoride [207] and tetrabutylphosphonium fluoride [208] have been used to prepare fluorohydrins from epoxides. Generation of a superacid is required for the ring opening of a perfluorinated oxirane [209] (Figure 3.42). 

Heating of 4-chloroquinolines with potassium fluoride (tetrabutylphosphonium fluoride) in DMSO affords only low yields of the corresponding 4-fluoro compounds [39, 40], however use of microwave irradiation (300 W) results in the formation of 2-fluoroquinolines from 2-chloroquinolines in 60-62 % yields [41], Replacement of the diaza group with the fluoride ion, the method which is widely used in heterocyclic chemistry, has also found its application to obtain fluo-roquinolines, as illustrated, for instance, by the syntheses of 3-fluoroquinoline from 3-aminoquinoline [42] and 3,5-difluoroquinoline from 3-fluoro-5-aminoquinoline, respectively [43], 3,7-Difluoro-6-methoxyquinoline 69, one of the key intermediates for the synthesis of antibacterial agents, has been obtained by the reaction of 3-amino-7-fluoro-6-methoxyquinoline with sodium nitrite in the presence of hydrogen borotetrafluoride (Scheme 26) [44],... 

In an attempt to produce TS-1 at low cost, alternative, cheaper sources of Ti and Si and other bases such as binary mixtures of (tetrabutylammonium and tetraethylammonium hydroxides), (tetrabutylphosphonium and tetraethylpho-sphonium hydroxides), (tetrapropylammonium bromide and ammonia, water, hexanediamine, n-butylamine, diethylamine, ethylenediamine, or triethanolamine) in place of TPAOH have been used (284—294). TS-1 was synthesized in the presence of fluoride ions but the material thus formed contained extraframework Ti species (295-297). 

Bromine fluoride can also be added by means of various reagents. The source of bromine is most often iV-bromoacetamide,171,172,198,251 iV-bromosuccinimide (NBS), 21 5,217.220.245-24-8. 254,696,698 i,3-dibromo-5,5-dimethylhydantoin (DBH).245,275,278 l-bromo-3,5,5-trimethyl-hydantoin(BTH),316 or bromine.108,197,217,227-229-261 The fluoride source is usually hydrogen fluoride,217,245,251,254 boron trifluoride,260 bromine trifluoride.227,261 xenon difluoride,108 tet-rabutylammonium dihydrogen trifluoride,694 tetrabutylphosphonium dihydrogen trifluo-... 

Benzyl trimethyl ammonium hydroxide Cetrimonium bromide Dimethyl diallyl ammonium chloride Laurtrimonium bromide Laurtrimonium chloride Methyl tributyl ammonium chloride Tetrabutyl ammonium bromide Tetrabutyl ammonium chloride Tetrabutyl ammonium fluoride Tetra-n-butyl ammonium hydrogen sulfate Tetra-n-butyl ammonium hydroxide Tetrabutyl ammonium iodide Tetrabutylphosphonium acetate, monoacetic acid Tetrabutylphosphonium bromide Tetrabutylphosphonium chloride Tetraethylammonium bromide Tetraethylammonium hydroxide Tetrakis (hydroxymethyl) phosphonium chloride Tetramethylammonium bromide Tetramethylammonium chloride Tetramethylammonium hydroxide Tetramethyl ammonium iodide Tetraphenyl phosphonium bromide Tetrapropyl ammonium bromide Tetrapropyl ammonium iodide Tributylamine Tributyl phosphine Tributyl (tetradecyl) phosphonium chloride Trioctyl (octadecyl) phosphonium iodide catalyst, phase-transfer Tetraethylammonium chloride Tetraoctylphosphonium bromide Tri-n-butyl methyl ammonium chloride Tri methyl phenyl ammonium hydroxide catalyst, phenolics Triethylamine... 

Uchibori Y, Umeno M, Yoshiokat H (1992) Nucleophilic fluorination of chlorinated N-heterocycles with tetrabutylphosphonium hydrogen fluoride and dihydrogen trifluoride. Heterocycles 34 1507-1509... 

Tetrabutylammonium chloride Tetrabutylammonium fluoride Tetrabutylammonium hydroxide Tetrabutylammonium iodide Tetrabutylammonium sulfate Tetrabutylphosphonium bromide... 

---