Unusual Nazarov Cyclization in Near-Critical Water
| Autor: | Olli Aaltonen, Jari Yli-Kauhaluoma, Martti Alkio, Juha Kaunisto, Tuomo Leikoski |
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| Rok vydání: | 2005 |
| Předmět: |
Carbonic acid
cyclization ketones Proton 010405 organic chemistry Near critical Chemistry Organic Chemistry Inorganic chemistry Nazarov reaction 010402 general chemistry Photochemistry 01 natural sciences cyclopentenones 6. Clean water 0104 chemical sciences chemistry.chemical_compound Yield (chemistry) Carbon dioxide Acetone Physical and Theoretical Chemistry |
| Zdroj: | Leikoski, T, Kaunisto, J, Alkio, M, Aaltonen, O & Yli-Kauhaluoma, J 2005, ' Unusual Nazarov cyclization in near-critical water ', Organic Process Research and Development, vol. 9, no. 5, pp. 629-633 . https://doi.org/10.1021/op050075t |
| ISSN: | 1520-586X 1083-6160 |
| Popis: | The Nazarov reaction of trans,trans-dibenzylidene acetone in near-critical water with or without additional carbon dioxide produces 2,3-diphenyl-2-cyclopentenone instead of the conventional Nazarov product, 3,4-disubstituted 2-cyclopentenone. The use of organic solvents and strong mineral acids, generally required for this reaction, is avoided by using water and carbonic acid as a proton source. After an optimization procedure, 38% yield of 2,3-diphenyl-2-cyclopentenone was obtained. The presence of carbon dioxide had a clear positive effect on yield. |
| Databáze: | OpenAIRE |
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