Issue 10, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp ®

Christopher J. Easton,*a   Graham A. Heath,a   C. Merrîcc M. Hughes,b   Connie K. Y. Lee,a   G. Paul Savage,c   Gregory W. Simpson,c   Edward R. T. Tiekink,b   George J. Vuckovica  and  Richard D. Webstera  

* Corresponding authors

a Research School of Chemistry, Australian National University, Canberra, Australia
E-mail: easton@rsc.anu.edu.au

b Department of Chemistry, University of Adelaide, Adelaide, Australia

c CSIRO Molecular Science, Bayview Ave, Clayton, Australia

Abstract

Isoxazoles substituted with an electron-withdrawing group at the 4-position undergo electrochemical and yeast-catalysed N–O bond cleavage. The electrolysis is much more efficient and, with acyl- and alkoxycarbonyl-substituted isoxazoles, it affords the enolised dicarbonylimine functionality characteristic of the herbicide Grasp®. Regioisomeric 4- and 5-substituted isoxazoles are accessible through nitrile oxide cycloaddition chemistry, using halogen as a steric auxiliary to control the regiochemistry of reaction. Crystal data for compounds 11 and 19b are presented.

Graphical abstract: Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp [ ] ®

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Article information

DOI
https://doi.org/10.1039/B008081K
Article type
Paper
Submitted
06 Oct 2000
Accepted
22 Mar 2001
First published
19 Apr 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1168-1174

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Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp ®

C. J. Easton, G. A. Heath, C. M. M. Hughes, C. K. Y. Lee, G. P. Savage, G. W. Simpson, E. R. T. Tiekink, G. J. Vuckovic and R. D. Webster, J. Chem. Soc., Perkin Trans. 1, 2001, 1168 DOI: 10.1039/B008081K

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