Poly(isoprenecarboxylates) from Glucose via Anhydromevalonolactone

A short and efficient synthesis of a series of isoprenecarboxylic acid esters and their corresponding polymers is presented. The base-catalyzed eliminative ring opening of anhydromevalonolactone (3) provides isoprenecarboxylic acid (6-H), which was further transformed to the isoprenecarboxylic acid...

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Bibliographic Details
Published in:ACS macro letters 2016-10, Vol.5 (10), p.1128-1131
Main Authors: Ball-Jones, Nicolas R., Fahnhorst, Grant W., Hoye, Thomas R.
Format: Article
Language:English
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Summary:A short and efficient synthesis of a series of isoprenecarboxylic acid esters and their corresponding polymers is presented. The base-catalyzed eliminative ring opening of anhydromevalonolactone (3) provides isoprenecarboxylic acid (6-H), which was further transformed to the isoprenecarboxylic acid esters. Reversible addition–fragmentation chain-transfer (RAFT) polymerization was used to synthesize high molecular weight (>100 kg mol–1) poly­(isoprenecarboxylates) with dispersities ( Đ ) of ca. 1.5. The glass transition temperatures (T g) and entanglement molecular weights (M e) of the poly­(isoprenecarboxylates) were determined and showed similar trends to the T g and M e values for analogous poly­(acrylate esters). These new glucose-derived materials could provide a sustainable alternative to poly­(acrylates).
ISSN:2161-1653
2161-1653
DOI:10.1021/acsmacrolett.6b00560