PubMed · 13060511
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C E BROOKE. 1953. The boric acid problem.. https://pubmed.ncbi.nlm.nih.gov/13060511/
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The chromatographic behavior of ephedrines (norephedrine, ephedrine, pseudoephedrine and methylephedrine) on a C18 column was studied with different concentrations of 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquids as the eluent at pH 3.0. The addition of ionic liquid has great effects on the separation of these basic compounds: decreasing band tailing, reducing band broadening, and improving resolution. The retention times of the analytes increase at first and then decrease with the increase in the concentration of ionic liquid. This effect may be attributed to the competition between imidazolium cations and the polar groups of the analytes for the silanol group on the alkylsilica surface, and also to the formation of weak bilayer electronic structure on the C18 column. Several ionic liquids with different alkyl substituents on the imidazolium cations or with different counterions as the eluents were compared.
[reaction: see text] A single-pot tandem catalytic diene diboration/carbonyl allylation reaction is described that uses a commercially available chiral diboron reagent. The chirality of the intermediate diboration adduct is transferred to the product in the carbonyl allylation reaction, thereby providing access to enantioenriched chiral products. Notably, the reaction allows for construction of a quaternary stereocenter and furnishes a synthetically versatile C-B bond in the reaction product.
Mixtures of t,t conjugated linoleic acid methylester (t,t CLA-Me) isomers were prepared from synthetic CLA, consisting of 47.8% t10,c12 CLA; 45.5% c9,t11 CLA; 2.0% t,t CLA; and 4.7% others, by methylation with BF(3)/methanol (designated TT-TC/CT) in conjunction with purification at -68 degrees C for 24 h. The amount or composition of the TT-TC/CT was greatly affected by the concentration of BF(3) in methanol and the duration of methylation. The methylation of 50 mg of synthetic CLA for 30 min with 1 mL of 7.0% BF(3)/methanol produced a TT-TC/CT (21.54 mg) with the composition of 1.3% t12,t14; 5.9% t11,t13; 42.7% t10,t12; 44.0% t9,t11; 5.0% t8,t10; and 1.1% t 7,t9 CLA, whereas the methylation for 60 min with 14.0% BF(3)/methanol produced a TT-TC/CT (28.62 mg) with the composition of t,t CLA isomers different from that of TT-TC/CT by methylation for 30 min with 7.0% BF(3)/methanol. A large quantity of TT-TC/CT (14.15 g) with the composition similar to that of TT-TC/CT prepared from 50 mg of synthetic CLA was also prepared from 25 g of synthetic CLA. The purity of TT-TC/CT samples was greater than 98%. These results suggest that TT-TC/CT with a purity greater than 98% was easily prepared from synthetic CLA by BF(3)-catalyzed methylation, and the amount and composition of t,t CLA isomers of TT-TC/CT samples could be controlled by methylation conditions.