Effect of ionic liquid organizing ability and amine structure on the rate and mechanism of base induced elimination of 1,1,1-tribromo-2,2-bis(phenyl-substituted)ethanes
| Autor: | Vitalba Pace, Francesca D'Anna, Vincenzo Frenna, Renato Noto |
|---|---|
| Přispěvatelé: | D'ANNA F, FRENNA V, PACE V, NOTO R |
| Rok vydání: | 2006 |
| Předmět: |
chemistry.chemical_classification
Steric effects Base (chemistry) Organic Chemistry Inorganic chemistry Kinetics Atmospheric temperature range ionic liquids elimination reaction base catalysis Biochemistry Medicinal chemistry chemistry.chemical_compound Elimination reaction chemistry Drug Discovery Ionic liquid Amine gas treating |
| Zdroj: | Tetrahedron. 62:1690-1698 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2005.11.061 |
| Popis: | The kinetics of the elimination reaction of 1,1,1-tribromo-2,2-bis(phenyl-substituted)ethanes into the corresponding 1,1-dibromo-2,2-bis(phenyl-substituted)ethenes induced by amines were studied in three room temperature ionic liquids ([BMIM][BF 4 ], [BMIM][PF 6 ], [BdMIM][BF 4 ]). In order to have information about reagent–ionic liquid interactions, the reaction was carried out over the temperature range (293.1–313.1 K). To study the effect of the amine on the rate and occurrence of the elimination reaction, several primary, secondary and tertiary amines with different structure (cyclic and acyclic), basicity and steric requirements were used. The data collected show that the reaction occurs faster in ionic liquids than in other conventional solvents. Furthermore, ionic liquids seem to be able to induce, for the studied reaction, a shift of mechanism from E1 cb (in MeOH) versus E2 (in ionic liquid). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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