Elimination Reactions of Aryl Furylacetates Promoted by R2 NH in MeCN: Effects of Base Solvent and β-Aryl Group on the Ketene-forming Transition State
| Autor: | Sang Yong Pyun, Bong Rae Cho, Byung Tae Kim, Man So Han, Kyu Cheol Paik |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Base (chemistry) Double bond 010405 organic chemistry Stereochemistry Aryl Kinetics Ketene General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Solvent Elimination reaction chemistry.chemical_compound chemistry Group (periodic table) |
| Zdroj: | Bulletin of the Korean Chemical Society. 38:1306-1309 |
| ISSN: | 1229-5949 |
| DOI: | 10.1002/bkcs.11285 |
| Popis: | Ketene-forming elimination from C4H3(O)CH2C(O)OC6H3-2-X-4-NO2 (1) promoted by R2NH in MeCN has been studied. The reactions produced elimination products and exhibited second-order kinetics with Bronsted β = 0.51, and |βlg| = 0.47–0.53, indicating that the reaction proceeds by the E2 mechanism via an E2-central transition state. Comparison of β, |βlg|, ΔH≠, and ΔS≠ values for R2NH-promoted eliminations from ArCH2C(O)OC6H3-2-X-4-NO2 reveals that the transition-state structures for Ar = furyl and thienyl are similar and more symmetrical than that for Ar = Ph. This outcome has been attributed to the greater double bond stabilizing ability of the former than that of the latter. |
| Databáze: | OpenAIRE |
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