The Synthesis of Bicyclo[2.2.2]octan-2,6-dione Revisited

Magnus Widegren; Melanie Dietz; Annika Friberg; Torbjörn Frejd; Bärbel Hahn-Hägerdal; Marie F. Gorwa-Grauslund; Mikael Katz

doi:10.1055/s-2006-942532

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Synthesis 2006(20): 3527-3530
DOI: 10.1055/s-2006-942532

PSP

The Synthesis of Bicyclo[2.2.2]octan-2,6-dione Revisited

Magnus Widegren^a, Melanie Dietz^a, Annika Friberg^a, Torbjörn Frejd*^a, Bärbel Hahn-Hägerdal^b, Marie F. Gorwa-Grauslund^b, Mikael Katz^b
^a Division of Organic Chemistry, Center for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, 22100 Lund, Sweden
Fax: +46(46)2224119; e-Mail: Torbjorn.Frejd@organic.lu.se;
^b Department of Applied Microbiology, Center for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, 22100 Lund, Sweden

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Publication History

Received 26 April 2006
Publication Date:
02 August 2006 (online)

Abstract
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Abstract

The cyclisation conditions for the formation of bicyclo[2.2.2]octan-2,6-dione (1) from 3-substituted cyclohexanones 2 and 3 have been re-investigated. Use of a medium consisting of isobutyric anhydride and trifluoroacetic acid resulted in a simplified and reproducible method for large-scale synthesis of this compound.

Key words

bicyclic compounds - cyclisations - diketones - carboxylic acids - anhydrides

References

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