ISSN:
0887-624X
Keywords:
phenyl[bis(2-pyridyl)]methyl methacrylate
;
optically active polymer
;
solvolysis
;
chiral stationary phase
;
anionic polymerization
;
(S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine
;
optical resolution
;
high performance liquid chromatography
;
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A novel monomer, phenyl[bis(2-pyridyl)]methyl methacrylate (PB2PyMA), was synthesized. The solvolysis rate of PB2PyMA measured in CDCl3-CD3 OD [1/1 (v/v)] by 1H-NMR spectroscopy at 35°C was much smaller than those of triphenylmethyl methacrylate (TrMA) and diphenyl-2-pyridylmethyl methacrylate (D2PyMA). PB2PyMA was anionically polymerized with the complexes of organolithiums with (-)-sparteine (Sp), (S,S)-(+)-and (R,R)-(-)-2,3-dimethoxy-1,4-bis(dimethylamino)butanes[(+)-and (-) -DDB], and (S)-(+)-1-(2-pyrrolidinylmethyl) pyrrolidine (PMP) in toluene at low temperature. The polymers obtained with Sp and DDB complexes showed low optical activity. PMP complexes, particularly that with N,N′-diphenylethylenediamine monolithium amide, were effective in synthesizing a polymer of high optical rotation ([α]25365 ∼ +1350°) which was comparable to those of poly(TrMA) and poly(D2PyMA) with one-handed helical structure. The optical rotation of poly(PB2PyMA) in a mixture of CHCl3 and 2,2,2-trifluoroethanol (9/1, v/v) slowly decreased with time. Optically active poly(PB2PyMA) coated on macroporous silica gel was able to resolve racemic compounds as a chiral stationary phase for high-performance liquid chromatography. © 1993 John Wiley & Sons, Inc.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/pola.1993.080311107
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