A nitro-hunsdiecker reaction: from unsaturated carboxylic acids to nitrostyrenes and nitroarenes.
[reaction: see text] 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 RCO(2)(*) by a NO(3)(*) radical followed by attack of a NO(2)(*) radical.
Organometallics and Catalysis Laboratory, Chemistry Department, Indian Institute of Technology, Kharagpur 721302, India.
Jaya Prakash
JP
Das
Pradipta
P
Sinha
Sujit
S
Roy