Nine functionalized dicationic ionic liquids were used to study the base catalyzed mononuclear rearrangement of (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole into the corresponding triazole at 363 K. Ionic liquids were characterized by the presence of 1-(1-imidazolylmethyl)- 3,5-di[1-(3′-octylimidazolylmethyl)]benzene cation, bearing on the structure a neutral imidazole unit as basic functionality. Besides anions generally used for monocationic ionic liquids, such as [Br−], [BF4 −], and [NTf2 −], also dianions having a rigid aromatic spacer such as 1,4-benzenedicarboxylate, 2,6- naphthalenedicarboxylate, and 1,5- and 2,6-naphthalenedisulfonate were taken into account. Furthermore, to have information about the effect deriving from the spacer rigidity also dianions such as 1,4- butanedicarboxylate and 1,6-hexanedicarboxylate were used. The basic strength of dicationic ionic liquids was determined using the Hammett indicator method. Data collected gave evidence that the outcome of the target reaction was affected by the nature of interactions operating between cation and anion of the ionic liquid used. Quite interestingly, solvent systems used had a good recyclability. Indeed, in some cases, they were reused for four cycles without significant loss in yield.

Rizzo, C., D'Anna, F., Marullo, S., & Noto, R. (2014). Task Specific Dicationic Ionic Liquids: Recyclable Reaction Media for the Mononuclear Rearrangement of Heterocycles. JOURNAL OF ORGANIC CHEMISTRY, 79, 8678-8683 [10.1021/jo501451t].

Task Specific Dicationic Ionic Liquids: Recyclable Reaction Media for the Mononuclear Rearrangement of Heterocycles

RIZZO, Carla;D'ANNA, Francesca;MARULLO, Salvatore;NOTO, Renato
2014

Abstract

Nine functionalized dicationic ionic liquids were used to study the base catalyzed mononuclear rearrangement of (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole into the corresponding triazole at 363 K. Ionic liquids were characterized by the presence of 1-(1-imidazolylmethyl)- 3,5-di[1-(3′-octylimidazolylmethyl)]benzene cation, bearing on the structure a neutral imidazole unit as basic functionality. Besides anions generally used for monocationic ionic liquids, such as [Br−], [BF4 −], and [NTf2 −], also dianions having a rigid aromatic spacer such as 1,4-benzenedicarboxylate, 2,6- naphthalenedicarboxylate, and 1,5- and 2,6-naphthalenedisulfonate were taken into account. Furthermore, to have information about the effect deriving from the spacer rigidity also dianions such as 1,4- butanedicarboxylate and 1,6-hexanedicarboxylate were used. The basic strength of dicationic ionic liquids was determined using the Hammett indicator method. Data collected gave evidence that the outcome of the target reaction was affected by the nature of interactions operating between cation and anion of the ionic liquid used. Quite interestingly, solvent systems used had a good recyclability. Indeed, in some cases, they were reused for four cycles without significant loss in yield.
Settore CHIM/06 - Chimica Organica
Rizzo, C., D'Anna, F., Marullo, S., & Noto, R. (2014). Task Specific Dicationic Ionic Liquids: Recyclable Reaction Media for the Mononuclear Rearrangement of Heterocycles. JOURNAL OF ORGANIC CHEMISTRY, 79, 8678-8683 [10.1021/jo501451t].
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10447/97806
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