Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5274785 | Tetrahedron Letters | 2011 | 4 Pages |
Abstract
The head-to-tail dimerization of methacrolein via the conjugate addition of methanol is catalyzed by various organic bases, such as an amine, phosphine, and N-heterocyclic carbene, to give 2,4-dimethyl-2-methoxymethylpentane-1,5-dial in moderate yields. Based on the interpretation of the key intermediates by electrospray ionization mass spectrometry, we propose a reaction mechanism involving the initial conjugate addition of the organic bases to methacrolein to generate a zwitterionic base followed by the activation of methanol.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Shin-ichi Matsuoka, Shintaro Shimakawa, Koji Takagi, Masato Suzuki,