Retention of Symmetry Versus Desymmetrization for Bicyclo[2.2.2]octenes in the Presence of a Bridgehead Amide Group

An efficient, microwave‐assisted and ionic‐liquid‐catalyzed esterification of bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid dianhydride derivatives into the corresponding tetraesters is presented. The latter were subjected to a base‐catalyzed isomerization reaction, which proceeded with the r...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2011-06, Vol.2011 (18), p.3368-3374
Main Authors: Hren, Jure, Perdih, Franc, Polanc, Slovenko, Kočevar, Marijan
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Bicyclic compounds
Chemistry
Exact sciences and technology
Green chemistry
Ionic liquids
Isomerization
Microwave chemistry
Organic chemistry
Preparations and properties
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Summary:An efficient, microwave‐assisted and ionic‐liquid‐catalyzed esterification of bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid dianhydride derivatives into the corresponding tetraesters is presented. The latter were subjected to a base‐catalyzed isomerization reaction, which proceeded with the retention of symmetry. Bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid tetraesters have been prepared in a green ionic‐liquid‐catalyzed microwave‐assisted reaction from the correspondingdianhydrides. The tetraesters isomerize in a base‐catalyzed isomerization reaction to give symmetrical products in high yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201100104