<b>Vinyltriphenylphosphonium salt-mediated preparation of thiophene-containing electron-poor alkenes from acetylenic esters, 2-thienylmethanol and triphenylphosphine</b>
Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and alkyl acetylenecarboxylates (methyl acetylenecarboxylate, ethyl acetylenecarboxylate and ethyl phenylacetylenecarboxylate) by 2-thienylmethanol leads to vinyltriphenylphosphonium salts, whic...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
Chemical Society of Ethiopia
2011-04-01
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| Series: | Bulletin of the Chemical Society of Ethiopia |
| Subjects: | |
| Online Access: | http://ajol.info/index.php/bcse/article/view/63370 |
| Summary: | Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and alkyl acetylenecarboxylates (methyl acetylenecarboxylate, ethyl acetylenecarboxylate and ethyl phenylacetylenecarboxylate) by 2-thienylmethanol leads to vinyltriphenylphosphonium salts, which undergo an addition-elimination reaction in CH<sub>2</sub>Cl<sub>2</sub> at room temperature to produce the corresponding <i>O</i>-vinylated alkenes <i>via</i> thiophene-containing phosphorus ylides intermediates in fairly high yields. The structural analysis of all products indicated that the reactions are regio- and stereoselective. |
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| ISSN: | 1011-3924 1726-801X |