Nef reaction

[1][2][3] The reaction was reported in 1894 by the chemist John Ulric Nef,[4] who treated the sodium salt of nitroethane with sulfuric acid resulting in an 85–89% yield of nitrous oxide and at least 70% yield of acetaldehyde.

However, the reaction was pioneered a year earlier in 1893 by Konovalov,[5] who converted the potassium salt of 1-phenylnitroethane with sulfuric acid to acetophenone.

Nef's original protocol, using concentrated sulfuric acid, has been described as "violent".

[9] Strong-acid hydrolysis without the intermediate salt stage results in the formation of carboxylic acids and hydroxylamine salts,[citation needed] but Lewis acids such as tin(IV) chloride[10] and iron(III) chloride[11] give a clean hydrolysis.

Alternatively, strong oxidizing agents, such as oxone,[12] ozone, or permanganates, will cleave the nitronate tautomer at the double bond to form a carbonyl and nitrate.