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RESEARCH PRODUCT

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

Vitalba PaceFrancesca D'annaVincenzo FrennaRenato Noto

subject

chemistry.chemical_classificationSteric effectsBase (chemistry)Organic ChemistryInorganic chemistryKineticsAtmospheric temperature rangeionic liquids elimination reaction base catalysisBiochemistryMedicinal chemistrychemistry.chemical_compoundElimination reactionchemistryDrug DiscoveryIonic liquidAmine gas treating

description

Abstract 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).

yearjournalcountryeditionlanguage
2006-02-01Tetrahedron
https://doi.org/10.1016/j.tet.2005.11.061