1996
DOI: 10.1021/ma951888s
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Stereochemical Control in the Anionic Polymerization of β-Butyrolactone Initiated with Alkali-Metal Alkoxides

Abstract: The anionic polymerization of (R)-β-butyrolactone initiated with either 18-crown-6 complexes of a potassium alkoxide or a simple carboxylate (reference initiator) proceeded with inversion of configuration. As a result (R)-β-butyrolactone formed an isotactic poly((S)-β-hydroxybutyrate) with these initiators at room temperature. Polymerization of (R,S)-β-butyrolactone under the same conditions gave an atactic polymer, but at lower temperatures the predominantly syndiotactic form of poly((R,S)-β-hydroxybutyrate) … Show more

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Cited by 74 publications
(59 citation statements)
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References 31 publications
(82 reference statements)
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“…Chemical synthesis of racemic [16][17][18][19] and chiral 20,21 poly(3-hydroxybutanoic acid) from b-butyrolactone monomer has been reported by some of us previously. Polymers thus obtained were characterized by 1 H and 13 C NMR, gel permeation chromatography, Fourier transform infrared spectroscopy and chemical analysis.…”
Section: Resultsmentioning
confidence: 97%
“…Chemical synthesis of racemic [16][17][18][19] and chiral 20,21 poly(3-hydroxybutanoic acid) from b-butyrolactone monomer has been reported by some of us previously. Polymers thus obtained were characterized by 1 H and 13 C NMR, gel permeation chromatography, Fourier transform infrared spectroscopy and chemical analysis.…”
Section: Resultsmentioning
confidence: 97%
“…Therefore, several attempts to use a catalyst based on much less toxic metal compounds are being undertaken [2,6,11,[22][23][24][25][26][27]. The anionic polymerization of β-butyrolactone had been widely studied [27][28][29][30][31][32][33][34][35][36][37][38][39][40], and in general polymers with low molecular weight were obtained. Relatively low toxic alkali metal hydrides are among the initiators used for this purpose [27], nevertheless, they have not been used so far for the synthesis of copolymers of (R,S)-BL and CL.…”
Section: Introductionmentioning
confidence: 99%
“…In contrast to coordination-insertion mechanism [16][17][18], the spectroscopic data suggest that the nucleophile -OR 0 ion of hybrid material attacks C=O carbon atom in e-CL. As it can be seen from literature survey for the base catalysts [19][20][21][22][23], this is an anionic mechanism.…”
Section: Resultsmentioning
confidence: 99%