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

…, GW Simpson, ERT Tiekink, GJ Vuckovic…

Index: Easton; Heath; Hughes; Lee; Savage; Simpson; Tiekink; Vuckovic; Webster Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 10 p. 1168 - 1174

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Citation Number: 24

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 ...