Oxazoles electrochemical reduction

Oxazoles (150) are reduced to oxazolines (151) by treatment with sodium and ethanol, and these products may then undergo further reduction to oxazolidines (152) and eventually to amino alcohols (153). Reduction with LAH follows the same course, as does electrochemical reduction. In the same way 2,2-bis(oxazoles) (154) when reacted with LAH afford diaminodiols (155). ... 

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... 

Tsveniashvili and co-workers acquired polarographic data for series of 2,4-disubstituted, 2,5-disubstituted, and 2,4,5-trisubstituted oxazoles and investigated the effects of substituents on the electrochemical reduction potential. They explained their results by two one-electron reversible steps to produce a dianion, which was then protonated. Rogers and co-workers described anion-pi radicals formed during electrochemical reduction of fused oxazoles, e.g., 2-phenylbenzox-azole. 

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