Tetra-n-butyl ammonium chloride

All the above reactions of PVC were performed homogeneously in DA-solvents such as HMPA, DMF and dimethylsulfoxide (DMSO). For the practical modification of PVC, the reaction must be conducted under more commercial conditions as in slurry water. As mentioned before, azidation of PVC did not occur in water. However, the reaction proceeded feasibly in water by addition of some cationic surfactant to give, e.g. 8-20% (DS) of azidated PVC at 80°C by use of tetra-n-butyl ammonium chloride (1 ). The use of cationic surfactant was also effective in organic solvents and attracted increased attention as the conception of "phase transfer catalyst" in organic chemistry developed. 

Tetra-N-butylammonium bromide. See Tetrabutyl ammonium bromide Tetrabutyl ammonium chloride CAS 1112-67-0 EINECS/ELINCS 214-195-7 Synonyms 1-Butanaminium, N,N,N-tributyl-, chloride Tetra-n-butyl ammonium chloride Empirical CieHseCIN... 

Tetra-n-butyl ammonium chloride. See Tetrabutyl ammonium chloride Tetrabutyl ammonium fluoride CAS 429-41-4 87749-50-6 (trihydrate) EINECS/ELINCS 207-057-2 Synonyms TBAF Tetra-n-butyl ammonium fluoride... 

FIGURE 6.11 Thermal desorption mass spectra of (a) tetra-n-butyl ammonium chloride and (b) glucose with NaCI. (Reprinted with permission from references 34 and 35, respectively). 

The addition of tetra(n-butyl)ammonium chloride to an aqueous solution of K[PtCl3(MeCN)l results in cation exchange and precipitation of [(M-Bu)4N][PtCl3(MeCN)] with KCl remaining in solution. The addition of sodium perchlorate to aqueous [Fe(bipy)3]Cl2 results in anion exchange and precipitation of [Fe(bipy)3][C104]2 with NaCl remaining in solution. 

The reaction of sodium azide with N-aryl chloroimines, obtained from benzanilides and thionyl chloride, to form 1,5-disubstituted tetrazoles is catalysed by tetra-n-butyl-ammonium bromide (Scheme 5.26, Table 5.40) [18] in variable yields, but generally <85%. 5-Butyl-2,3-diphenyltetrazolium salts have also been used as catalysts [18, 19]. 1,5-Disubstituted tetrazoles are also obtained from a one-pot sequential reaction of carbodimides with sodium azide and an aroyl chloride in the presence of tetra-n-butylammonium chloride [20]. 5-Chlorotetrazoles are obtained from the catalysed reaction of aryldichloroisocyanides with sodium azide (Scheme 5.26) [21],... 

Optimum yields of (3-vinyl-y-butyrolactols from the Pd(II) promoted reaction of vinyl triflates with Z-but-2-en-l,4-diol (Scheme 6.33) are attained when tetra-n-butylammonium chloride is added (47]. The lactol is conveniently oxidized to the lactone with celite-supported silver carbonate. The corresponding arylbutyrolactols are obtained in high yield (70-80%) from an analogous reaction of iodoarenes with the enediol. The yields of 2-alkenyl-2,5-dihydrofurans, resulting from the Pd(0) catalysed reaction of cyclic alkynylcarbonates with acrylic esters via tandem C-C and C-0 bond forming reactions, are enhanced by the presence of tetra-n-butyl-ammonium fluoride (e.g. Scheme 6.33) (48]. 

E-2-bromomethyleneglutaric esters (>70%) have been obtained from the corresponding 2-bromo-2-bromomethylglutarates using a 25% excess tetra-n-butyl-ammonium fluoride in HMPA [24], A similar procedure converts dimethyl 2-bromo-2-bromomethylsuccinate into dimethyl Z-2-bromomethylenefumarate [25], whereas methyl 2,2-bis(bromomethyl)ethanoate yields the 2-bromomethyl-propenoate when reacted with aqueous sodium hydroxide in the presence of benzyl-triethylammonium chloride [26]. No hydrolysis of the ester is evident at 0°C, but becomes apparent at 25 °C. 

MACROLiDEs Chloiomethyl methyl sulfide. Dialkylhoryl trifluori imethanesulfonate. Di-n-hutyltin oxide. Dichloroketene. 4-Di-methylamino-3-butyi e-2-one. Keteny 1 i-dene triphenylphospl orane. Tetra-n-butyl-ammonium fluoride. 1,1,6,6-Tetra-n-butyI-1,6-distanna-2,5,7, lO-tetraoxycyclodecane. Tetrakisftriphenylphdsphine)-palladium. N,N,N,Nl-Tetramethylchloro-formamidinium chloride. 

Stearic acid titration is performed by a potentiometric method in dimethylformamide and in the presence of tetra-n-butyl ammonium hydroxide (7). The consumption of carboxylates vs. time is deduced from chloride and stearic acid titration according to the stoichiometry of Reaction 1 where Me is Zn or Ca and R is the stearic group. 

Fig. 1.1 Electrosteric (i.e. electrostatic with the halide anions located between the positively charged NP surface and the tetra-N-butyl ammonium cations and steric with the tetra-N-butyl ammonium cation) stabilization of metal NPs obtained by reduction of a metal chloride salt in the presence of a tetra-N-butyl ammonium cation (Bonnemann-type synthesis of Eq. (1.1)). The presence of...

Oxidation of alcohols. Alcohols are oxidized in generally high yield by aqueous sodium hypochlorite under phase-transfer catalysis with tetra-n-butyl-ammonium bisulfate. Benzene, chloroform, and methylene chloride can serve as the organic phase, but ethyl acetate is the solvent of choice. 

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... 

The catalytically active nano-sized palladium particles can be also stabilized by using triphenylphosphine and a polar solvent like in method L Similar to methods A, B and F, the palladium(O) catalyst, in situ prepared from palladium(ll) chloride and triphenylphosphine (only 1.3 eq. to Pd) and additionally stabilized with tetra-n-butyl ammonium bromide (as PTC) and polar reaction solvent, DMF, effectively accelerates the homo-couplings of aryl bromides and chlorides with zinc as the ultimate reductant to give the respective biaryls in good yields. Once again, the reductive dehalogenation as the only side-reaction occurs in considerable amount (max. 20%) [64]. 

Methyl esters undergo trans-esterification with the quaternary ammonium salts at high temperature and the reaction has been used with some effect for the preparation of, for example, n-butyl esters by heating the methyl ester with tetra-n-butylammo-nium chloride at 140°C [31]. Optimum yields (>75%) are obtained in HMPA or in the absence of a solvent. A two-step (one-pot) trans-esterification under phase-transfer catalysed conditions in which the carboxylate anion generated by initially hydrolysis of the ester is alkylated has been reported for Schiff s bases of a-amino acids [32] and for A-alkoxycarbonylmethyl [1-lactams [33]. Direct trans-esterification of methyl and ethyl esters with alcohols under basic catalytic conditions occurs in good yield in the presence of Aliquat [34, 35]. 

PHASE-TRANSFER CATALYSTS Adogen. Benzyldimethyldodecylammonium bromide. Benzyltriethylammonium chloride. N-Dodeoylpentamethylphosphotamide. Hexadecyl-trlbutylphosphonium bromide. Methyltricapiylylaminonium chloride. Tetra- -butyl-ammonium chloride. 

In a typical n.m.r. titration experiment the addition of one equivalent of tetra-butyl ammonium chloride to a d -dimethyl sulphoxide solution of L led to substantial shifts of the receptor s proton signaSs (Figure 1). The values of the proton resonances are given in Table 1 together with the observed shifts. 

Ac, acetyl AIBN, azobis(isobutanonitrile) All, allyl AR, aryl Bn, benzyl f-BOC, ferf-butoxycarbonyl Bu, Butyl Bz, benzoyl CAN, ceric ammonium nitrate Cbz, benzyloxycarbonyl m-CPBA, m-chloroperoxybenzoic acid DAST, diethylaminosulfur trifluoride DBU, l,8-diazabicyclo[5.4.0]undec-7-ene DCC, /V. /V - d i eye I oh e x y I c ar bo -diimide DCM, dichloromethyl DCMME, dichloromethyl methyl ether DDQ, 2,3-dichloro-5,6-dicyano-l,4-benzoquinone DEAD, diethyl azodicarboxylate l-(+)-DET, L-(+)-diethyl tartrate l-DIPT, L-diisopropyl tartrate d-DIPT, D-diisopropyl tartrate DMAP, 4-dimethylaminopyridine DME, 1,2-dimethoxyethane DMF, /V./V-dimethylformamide DMP, 2,2-dimethoxypropane Et, ethyl Im, imidazole KHMDS, potassium hexamethyldisilazane Me, methyl Me2SO, dimethyl sulfoxide MOM, methoxymethyl MOMC1, methoxymethyl chloride Ms, methylsulfonyl MS, molecular sieves NBS, N-bromosuccinimide NIS, /V-iodosuccinimide NMO, /V-methylmorpho-line N-oxide PCC, pyridinium chlorochromate Ph, phenyl PMB, / -methoxvbenzyl PPTs, pyridiniump-toluenesulfonate i-Pr, isopropyl Py, pyridine rt, room temperature TBAF, tetrabutylammonium fluoride TBS, ferf-butyl dimethylsilyl TBDMSC1, f-butylchlorodimethylsilane Tf, trifhioromethylsulfonyl Tf20, trifluoromethylsulfonic anhydride TFA, trifluoroacetic acid THF, tetrahydrofuran TMS, trimethylsilyl TPAP, tetra-n-propylammonium perruthenate / -TsOH. / -toluenesulfonic acid... 

Ionic liquids [e.g. l-ethyl-3-methylimidazolium triflate (mp. —9 C) l-n-butyl-3-methyl-pyridinium chloride (mp. 98 °C) tetra- -butyl-ammonium bromide (mp. 130 °C)]... 

Polymerization of I. I was polymerized in flame-dried equipment under N 2 at -40 °C as follows. A 25-mL round-bottom flask equipped with a poly(tetra-fluoroethylene) (Teflon)-covered magnetic stirring bar and rubber septum was charged with I (1.2 g, 10.9 mmol) (5, 6), THF (10 mL), and either HMPA (5 drops) or TMEDA (5 drops). n-Butyllithium (0.8 mL, 1.2 M, 0.96 mmol) was added slowly to this mixture. The mixture quickly became thick. The mixture was stirred for 1 h at -40 °C and then warmed to -20 °C, and saturated aqueous ammonium chloride was added. The organic layer was separated, washed with brine and water, and dried over molecular sieves (4 A). After filtration, the solvent was removed by evaporation under vacuum 1.10 g (92% yield) of polymer was isolated. The yields of polymer ( 2%) and their spectral properties were identical regardless of whether HMPA or TMEDA was used as cocatalyst. With n-butyllithium-TMEDA, a polymer with Mw and Mn of 158,000 and 69,000, respectively, was obtained, whereas with n-butyl-lithium-HMPA, a polymer with My, and M of 120,000 and 30,400, respectively, was isolated. 

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