Nef reaction

Not to be confused with Nef isocyanide reaction or Nef synthesis.

Nef reaction
Named after John Ulric Nef
Reaction type Substitution reaction
Identifiers
Organic Chemistry Portal nef-reaction
RSC ontology ID RXNO:0000157

In organic chemistry, the Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane (R−NO2) to an aldehyde (R−CH=O) or a ketone (R2C=O) and nitrous oxide (N2O). The reaction has been the subject of several literature reviews.[1][2][3]

The Nef reaction: 1. Salt of a nitroalkane 3. Ketone 4. Nitrous oxide
The Nef reaction:
1. Salt of a nitroalkane
3. Ketone
4. Nitrous oxide

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.

  1. ^ Noland, Wayland E. (1955). "The NEF Reaction". Chemical Reviews. 55 (1): 137–155. doi:10.1021/cr50001a003.
  2. ^ Pinnick, Harold W. (1990). "The Nef Reaction". In Paquette, Leo A. (ed.). Organic Reactions Volume 38 (1st ed.). New York: Wiley. pp. 655–792. doi:10.1002/0471264180.or038.03. ISBN 9780471515944.
  3. ^ Grierson, David S.; Husson, Henri-Philippe (1991). "4.7 – Polonovski- and Pummerer-type Reactions and the Nef Reaction". In Trost, Barry; Fleming, Ian (eds.). Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Synthesis, Volume 6 (1st ed.). New York: Pergamon. pp. 909–947. doi:10.1016/B978-0-08-052349-1.00175-X. ISBN 9780080359298.
  4. ^ Nef, John Ulric (1894). "Ueber die Constitution der Salze der Nitroparaffine". Justus Liebigs Annalen der Chemie. 280 (2–3): 263–291. doi:10.1002/jlac.18942800209.
  5. ^ Konovalov.,: J. Russ. Phys. Chem. Soc. 2 1893, 6(I), 509.