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Highly Efficient Catalysis of Retro‐Claisen Reactions: From a Quinone Derivative to Functionalized Imidazolium Salts
Author(s) -
Visbal Renso,
Laguna Antonio,
Gimeno M. Concepción
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201505095
Subject(s) - chemistry , catalysis , nucleophile , quinone , derivative (finance) , alcohol , claisen rearrangement , bond cleavage , medicinal chemistry , organic chemistry , lewis acids and bases , nucleophilic addition , ring (chemistry) , cleavage (geology) , materials science , fracture (geology) , financial economics , economics , composite material
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.