Synthesis and application of α-carbonyl nitrile oxides

Abstract

A novel strategy for synthesizing α-carbonyl nitrile oxides has been developed utilizing tert-butyl nitrite (TBN) as a 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 experiments and the syntheses of some bioactive molecules. A plausible free radical mechanism involving α-nitro ketone intermediates is proposed based on mechanistic investigations.