Aminal-catalyzed isomerization of and addition to dimethyl maleate
โ Scribed by A.Gilbert Cook; Andrea B Voges; Aster E Kammrath
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 178 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The amine moiety of aminals adds to dimethyl maleate via azomethine ylid intermediates. The products of this reaction, in turn, cause dimethyl maleate to isomerize to dimethyl fumarate.
๐ SIMILAR VOLUMES
Recently, the base-catalyeed isomarlcations ethers1 \*\* and l-to 2-olafI& bave baen reported of ally1 to propenyl to be hiShly selective in yialding the a-isomers. We wish to report on a similar isomariratioa of tert'kary ally1 ulnes which appears to be very much less selective under coadltions ess
## Abstract For Abstract see ChemInform Abstract in Full Text.
Diesters of (E)-2-alkylidenesuccinic acids obtained by conjugate addition of nitroalkanes to dimethyl maleate can be selectively monohydrolyzed at the more reactive carboxyl group to the corresponding half-ester. Alternatively, total hydrolysis to the diacid allows a subsequent selective methyl este