Synthesis of stereoregular poly(alkyl malolactonates)
- 1 December 1986
- journal article
- research article
- Published by Wiley in Makromolekulare Chemie. Macromolecular Symposia
- Vol. 6 (1), 285-303
- https://doi.org/10.1002/masy.19860060128
Abstract
Optically pure methyl, ethyl, isopropyl, and benzyl (R)-malolactonate were prepared from (S)-(-)-malic acid and were polymerized in the bulk with tetraethylammonium benzoate as the initiator to yield high-molecular-weight, crystalline polymers. The optical purity of methyl and benzyl malolactonate was determined by 1H NMR spectroscopy of the β-lactone complexed with a chiral europium shift reagent. Enantiomeric excesses of 100% were found (the experimental error was 3%). Optically active poly(β-malic acid) was obtained from optically active poly[benzyl (S)-malate] by catalytic hydrogenolysis of the pendent benzyl esters. Ethyl and benzyl (R)-malolactonate were also copolymerized, and the benzyl esters of the resulting copolymer were converted into carboxylic acid units by hydrogenolysis.Keywords
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