Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivatives
Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by alcohols (2-methanol thiophen, 3-methanol thiophen, 1,1,1,3,3,3-hexafluoro-2-propanol and [4-(trifluoromethyl)-phenyl]methanol) leads to vinyltriphenylpho...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Chemical Society of Ethiopia
2012-12-01
|
| Series: | Bulletin of the Chemical Society of Ethiopia |
| Subjects: | |
| Online Access: | http://www.ajol.info/index.php/bcse/article/view/72971 |
| Summary: | Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by alcohols (2-methanol thiophen, 3-methanol thiophen, 1,1,1,3,3,3-hexafluoro-2-propanol and [4-(trifluoromethyl)-phenyl]methanol) leads to vinyltriphenylphosphonium salts, which undergo Michael addition reaction with conjugate base to produce the corresponding stabilized phosphorus ylides. Wittig reaction of the stabilized phosphorus ylides with ninhydrin leads to the corresponding densely functionalized 2<i>H</i>-indeno[2,1-<i>b</i>]furans in fairly good yields.DOI: http://dx.doi.org/10.4314/bcse.v26i1.18 |
|---|---|
| ISSN: | 1011-3924 1726-801X |