Computational study on the mechanism of the three-component reaction of dimethylacetylene dicarboxylate and triphenylphosphine with 2-acetylbutyrolactone
| العنوان: | Computational study on the mechanism of the three-component reaction of dimethylacetylene dicarboxylate and triphenylphosphine with 2-acetylbutyrolactone |
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| المؤلفون: | Sakineh Asghari, Samaneh Ramezani, Mina Haghdadi |
| المصدر: | Canadian Journal of Chemistry. 93:666-672 |
| بيانات النشر: | Canadian Science Publishing, 2015. |
| سنة النشر: | 2015 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Cyclobutene, Chemistry, Organic Chemistry, General Chemistry, Photochemistry, Catalysis, chemistry.chemical_compound, Ylide, Intramolecular force, Wittig reaction, Density functional theory, Conrotatory and disrotatory, Triphenylphosphine, Derivative (chemistry) |
| الوصف: | The molecular mechanism of the three-component reaction of triphenylphosphine, dialkyl acetylene dicarboxylate, and 2-acetylbutyrolactone to synthesize the stabilized phosphorus ylide and 1,3-butadiene derivative via the intramolecular Wittig reaction has been investigated using the density functional theory method at the B3LYP/6-31G level of theory. Two possible reaction pathways have been characterized in detail to form the cyclobutene intermediate and in the next step; the cyclobutene intermediate undergoes the conrotatory ring-opening reaction to produce the 1,3-butadiene derivative along two possible pathways. The calculated results indicate that two pathways (pathways II and II-a) are the most energy favorable among all of the pathways, so they occur more than do the others. Moreover, the phosphorus ylide is more stable than the corresponding 1,3-butadiene, demonstrating that the intramolecular Wittig reaction could not easily occur at room temperature, which is in agreement with the experimental results. |
| تدمد: | 1480-3291 0008-4042 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_________::22d3fa5b3c6f89e35d7c9f321c3659adTest https://doi.org/10.1139/cjc-2014-0475Test |
| حقوق: | CLOSED |
| رقم الانضمام: | edsair.doi...........22d3fa5b3c6f89e35d7c9f321c3659ad |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 14803291 00084042 |
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