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...
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| Format: | Article |
| Language: | English |
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Chemical Society of Ethiopia
2012-12-01
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| Series: | Bulletin of the Chemical Society of Ethiopia |
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| Online Access: | http://www.ajol.info/index.php/bcse/article/view/72971 |
| _version_ | 1819241349390532608 |
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| author | Yavar Ahmadi Sadegh Salmanpour Ali Ramazani |
| author_facet | Yavar Ahmadi Sadegh Salmanpour Ali Ramazani |
| author_sort | Yavar Ahmadi |
| collection | DOAJ |
| description | 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 |
| first_indexed | 2024-12-23T14:22:30Z |
| format | Article |
| id | doaj.art-cbae164fb47249ff9351d8d6ace9884b |
| institution | Directory Open Access Journal |
| issn | 1011-3924 1726-801X |
| language | English |
| last_indexed | 2024-12-23T14:22:30Z |
| publishDate | 2012-12-01 |
| publisher | Chemical Society of Ethiopia |
| record_format | Article |
| series | Bulletin of the Chemical Society of Ethiopia |
| spelling | doaj.art-cbae164fb47249ff9351d8d6ace9884b2022-12-21T17:43:45ZengChemical Society of EthiopiaBulletin of the Chemical Society of Ethiopia1011-39241726-801X2012-12-01261153158Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivativesYavar AhmadiSadegh SalmanpourAli RamazaniProtonation 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.v26i1.18http://www.ajol.info/index.php/bcse/article/view/72971Electron-poor alcoholAcetylenic estersNinhydrinIntramolecular Wittig reactionVinyltriphenylphosphonium salt |
| spellingShingle | Yavar Ahmadi Sadegh Salmanpour Ali Ramazani Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivatives Bulletin of the Chemical Society of Ethiopia Electron-poor alcohol Acetylenic esters Ninhydrin Intramolecular Wittig reaction Vinyltriphenylphosphonium salt |
| title | Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivatives |
| title_full | Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivatives |
| title_fullStr | Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivatives |
| title_full_unstemmed | Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivatives |
| title_short | Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivatives |
| title_sort | synthesis of stabilized phosphorus ylides from electron poor alcohols and their applications in the preparation of 2 5 dihydrofuran derivatives |
| topic | Electron-poor alcohol Acetylenic esters Ninhydrin Intramolecular Wittig reaction Vinyltriphenylphosphonium salt |
| url | http://www.ajol.info/index.php/bcse/article/view/72971 |
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