ISSN:
0887-624X
Keywords:
optically-active polyurethane
;
chiral stationary phase
;
racemate
;
direct resolution
;
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Optically-active polyurethanes (2a-2c) were prepared by polyaddition reaction of diamide (1a, 1b) and diester (1c) derivatives of chiral coumarin dimer with 4,4′-diphenylmethane diisocyanate (MDI) in chloroform and methyl ethyl ketone, respectively. The inherent viscosity of the polyurethanes are between 0.13 and 0.21 dL/g in N,N-dimethylacetamide (DMAc) at 30°C. Treated silica gels were absorbed with ca. 25 wt % of the polyurethanes, and packed as chiral stationary phases for direct optical resolution of 16 racemates with aromatic groups by high-performance liquid chromatography (HPLC). Polyurethanes 2a and 2b, obtained from diamide derivatives, show efficient resolution ability to some of the racemates (α = 1.06-1.79), especially the atropic (R5) and trans (R6-R9) isomers. The recognition ability of the polyurethanes can be attributed to the simultaneous aromatic stacking and hydrogen-bonding interactions with racemates. © 1992 John Wiley & Sons, Inc.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/pola.1992.080301305
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