A nitro-Hunsdiecker reaction: From unsaturated carboxylic acids to nitrostyrenes and nitroarenes

[GRAPHICS] The nitrodecarboxylation of aromatic alpha,beta-unsaturated carboxylic acids and ring-activated benzoic acids can be achieved using nitric acid (3 equiv) and catalytic AIBN (2 mol %) in MeCN. From the effect of various additives, the nitrodecarboxylation is postulated to involve the generation of an acyloxy radical RCO2. by a NO3* radical followed by attack of a NO2* radical.