Tetra-n-butyl*ammonium fluoride

Phase-transfer catalysis can be used to mimic high dilution reaction conditions and has been utilized to good effect in the synthesis of large ring lactones [67J. Macrocyclic nitrolactones have also been obtained by rearrangement of 2-(3-hydroxy-propyI)-2-nitrocycloalkanones using a stoichiometric amount of tetra-n-butyl-ammonium fluoride [68]. 

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. 

N-Sulphonyl azoles are deprotected by a stoichiometric amount of tetra-n-butyl-ammonium fluoride in THF in good yields (>70%) [19]. 

They chose the TBDMS derivatives for reducing the polarity of hydroxyl groups of hydroxy fatty acid PNB esters because the TBDMS derivatives were resistant to hydrolysis, stable in common organic solvents, and changed the adsorption TLC and RP-HPLC retention of PNB hydroxy fatty acids more than smaller siloxy groups and because the TBDMS groups could easily be removed by fluoride ions (sodium fluoride or tetra-n-butyl ammonium fluoride) to free... 

However, an efficient synthesis of the spirovetivane-sesquiterpene a-Vetispirene 392 was achieved initiating the cleavage of the silicon-cyclopropane carbon bond of 160 by fluoride ion. This was effected with anhydrous tetra-n-butyl ammonium fluoride in THF solution containing acetone at reflux temperature for 10 hr. The pentadienyl anion 387 thus generated experienced highly regioselective addition of acetone at the... 

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. 

TBAI = tetra(n-butyl)ammonium iodide TBAF = tetra(n-butyl)ammonium fluoride... 

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... 

Tetra-n-butyl ammonium fluoride. See Tetrabutyl ammonium fluoride Tetrabutylammonium hydrogen sulfate. See Tetra-n-butyl ammonium hydrogen sulfate Tetra-n-butyl ammonium hydrogen sulfate CAS 32503-27-8 EINECS/ELINCS 251-068-5 Synonyms 1-Butanaminium, N,N,N-tributyl-, sulfate (1 1) TBAHS Tetrabutylammonium hydrogen sulfate N,N,N-Tributyl-1-butanaminium sulfate (1 1)... 

Mitsunobu Reactions. The readily obtained Ai-Boc derivative of SES-NH2 is sufficiently acidic that it can participate effectively in Mitsunobu reactions with alcohols. Both Ai-protecting groups can be efficiently removed from the product amine derivative under different conditions (tetra-n-butyl ammonium fluoride or trifluoroacetic acid for SES or Boc, respectively) and without racemization. ... 

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