Catalytic Dimerization of Crotonates

A room-temperature dimerization of crotonates into 2-ethylidene-3-methylpentanedioates provides a sustainable route to difunctional monomers for step-growth polymerizations. We report two such dimerizations: (1) an organocatalytic dimerization using the N-heterocyclic carbene 1,3-diisopropyl-4,5-dim...

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Bibliographic Details
Published in:ACS catalysis 2015-09, Vol.5 (9), p.5328-5332
Main Authors: Flanagan, James C. A, Kang, Eun Joo, Strong, Nathaniel I, Waymouth, Robert M
Format: Article
Language:English
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Summary:A room-temperature dimerization of crotonates into 2-ethylidene-3-methylpentanedioates provides a sustainable route to difunctional monomers for step-growth polymerizations. We report two such dimerizations: (1) an organocatalytic dimerization using the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (I i Pr2Me2) and (2) a rapid dimerization (under 15 s to full conversion) using potassium t-butoxide in THF. In addition to unsaturated diesters, the resulting dimers can be easily converted to other step-growth monomers; namely, their corresponding diacids and saturated diesters.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.5b00930