Nef synthesis

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

Nef synthesis
Named after	John Ulric Nef
Reaction type	Coupling reaction
Identifiers
RSC ontology ID	RXNO:0000506

In organic chemistry, Nef synthesis is the addition of sodium acetylides to aldehydes and ketones to yield propargyl alcohols.^{[1][2][3][4][5][6]} It is named for John Ulric Nef, who discovered the reaction in 1899.

This process is often erroneously referred to as the Nef reaction,^[4][7][8][9] which is an unrelated chemical transformation discovered by the same chemist.

See also

• Favorskii reaction
• Alkynation

References

1. Nef, John Ulric (1899). "Ueber das Phenylacetylen, seine Salze und seine Halogensubstitutionsproducte" (PDF). Justus Liebigs Annalen der Chemie. 308 (3): 264–328. doi:10.1002/jlac.18993080303.
2. Johnson, A. W. (1946). The Chemistry of the Acetylenic Compounds (1st ed.). London: Arnold. p. 11. Retrieved 25 February 2016.
3. Hurd, Charles D.; McPhee, Warren D. (1947). "Condensation of Acetylene with Acetone and Other Ketones". Journal of the American Chemical Society. 69 (2): 239–241. doi:10.1021/ja01194a018.
4. Oroshnik, William; Mebane, Alexander D. (1949). "The Nef Reaction with α,β-Unsaturated Ketones". Journal of the American Chemical Society. 71 (6): 2062–2065. doi:10.1021/ja01174a048.
5. Raphael, Ralph Alexander (1955). Acetylenic Compounds in Organic Synthesis (1st ed.). London: Butterworths. p. 10. Retrieved 25 February 2016.
6. Coffman, Donald D. (1940). "Dimethylethhynylcarbinol". Organic Syntheses. 40: 20. doi:10.15227/orgsyn.020.0040.
7. Viehe, Heinz Günter (1969). Chemistry of Acetylenes (1st ed.). New York: Marcel Dekker, inc. pp. 207–241. doi:10.1002/ange.19720840843.
8. Wolfrom, Melville L. (1960). "John Ulric Nef: 1862—1915". Biographical Memoirs (PDF) (1st ed.). Washington, DC: National Academy of Sciences. p. 218. Retrieved 24 February 2016.
9. Smith, Michael B.; March, Jerry (2007). "Chapter 16. Addition to Carbon–Hetero Multiple Bonds". March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.). Hoboken, New Jersey: John Wiley & Sons, Inc. pp. 1359–1360. doi:10.1002/9780470084960.ch16. ISBN 9780471720911.