Isoxazoles electrochemical reduction

Anion-radicals generated from oxazole and isoxazole in an argon matrix were shown, like their counterpart from furan, to have undergone ring scission. Consistent with this, various attempts to reduce isoxazoles polarographically in both protic and aprotic media have also resulted in the loss of ring integrity, and indeed the reduction process has always involved two electrons. However, electrochemical reduction of... 

Other reagents recommended for the reduction of isoxazoles to 1,3-enaminoketones include samarium diiodide, molybdenum hexacarbonyl in aqueous acetonitrile, and diiron nonacarbonyl in water. Electrochemical methods have also been employed." A particularly mild method involves reaction with the reduced form of the coenzyme lipoamide (LA2) complexed with iron(II). Birch reduction (sodium and... 

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