Synthesis and Application of α-Carbonyl Nitrile Oxides

A facile strategy of α-carbonyl nitrile oxides has been developed, utilizing tert-butyl nitrite (TBN) as nitrogen source. A diverse range of α-carbonyl furoxans and α-carbonyl isoxazoles have been obtained in good to excellent yields, including aromatic and aliphatic products. The practical utility of this protocol has been demonstrated in gram-scale experiment and synthesis of some bioactive molecules. A plausible free radical mechanism containing α-nitro ketone intermediates was proposed based on mechanistic investigations.