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Universidad de la Costa, CUC. Calle 58 # 55 - 66. Barranquilla, Colombia. 336 22 00. repositorioredicuc@cuc.edu.co. Corporación Universidad de la Costa.

Highly Efficient Catalysis of Retro-Claisen Reactions: From a Quinone Derivative to Functionalized Imidazolium Salts

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Highly Efficient Catalysis of Retro (7.366Kb)
Date
2016
Author
Visbal Acevedo, Renso Raul
Laguna, Antonio
Gimeno, María Concepción
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URI: http://hdl.handle.net/11323/940
Citar con DOI: DOI: 10.1002/chem.201505095

Abstract

A new and efficient method for the preparation of several imidazolium salts containing an ester group in the C4 position of the aromatic ring through a retro-Claisen reaction pathway between a quinone derivative and several alcohols is described. This new organic transformation proceeds in the absence of a catalyst, but it is greatly catalyzed by different Lewis acids, especially with AgOAc at a very low catalyst loading and in very short reaction times. The process takes place by the nucleophilic attack of the carbonyl groups by the alcohol functionality, thus promoting a double C-C bond cleavage and C-H and C-O bond formation. This reaction represents the first example of this type between a quinone derivative and alcohols. A new and efficient method for the preparation of several imidazolium salts containing an ester group in the C4 position of the aromatic ring through a retro-Claisen reaction pathway is described. This new organic transformation takes place by the nucleophilic attack of an alcohol functionality over the carbonyl groups, thus promoting a double C-C bond activation (see scheme; Mes=mesityl).
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Universidad de la Costa, CUC

  • Calle 58 # 55 - 66. Barranquilla, Colombia

  • 336 22 00

  • repositorioredicuc@cuc.edu.co

Corporación Universidad de la Costa CUC, Personería Jurídica con Resolución No. 352 del 23 de abril de 1971 y reconocida como Universidad mediante resolución 3235 del 28 de marzo de 2012 expedida por el MEN. Institución de Educación Superior sujeta a inspección y vigilancia por el Ministerio de Educación Nacional.

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