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Nef synthesis

In organic chemistry, Nef synthesis is the addition of sodium acetylides to aldehydes and ketones to yield propargyl alcohols. It is named for John Ulric Nef, who discovered the reaction in 1899.

This process is often erroneously referred to as the Nef reaction, which is an unrelated chemical transformation discovered by the same chemist.

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See also

References

  1. Nef, John Ulric (1899). "Ueber das Phenylacetylen, seine Salze und seine Halogensubstitutionsproducte". Justus Liebigs Annalen der Chemie. 308 (3): 264–328. doi:10.1002/jlac.18993080303. https://zenodo.org/record/1427517 ↩

  2. Johnson, A. W. (1946). The Chemistry of the Acetylenic Compounds (1st ed.). London: Arnold. p. 11. ISBN 978-0-598-99095-2. Retrieved 25 February 2016. {{cite book}}: ISBN / Date incompatibility (help) 978-0-598-99095-2 ↩

  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. /wiki/Doi_(identifier) ↩

  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. /wiki/Doi_(identifier) ↩

  5. Raphael, Ralph Alexander (1955). Acetylenic Compounds in Organic Synthesis (1st ed.). London: Butterworths. p. 10. Retrieved 25 February 2016. http://babel.hathitrust.org/cgi/pt?id=mdp.39015064396958;view=1up;seq=1 ↩

  6. Coffman, Donald D. (1940). "Dimethylethhynylcarbinol". Organic Syntheses. 40: 20. doi:10.15227/orgsyn.020.0040. /wiki/Doi_(identifier) ↩

  7. 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. /wiki/Doi_(identifier) ↩

  8. Viehe, Heinz Günter (1969). Chemistry of Acetylenes (1st ed.). New York: Marcel Dekker, inc. pp. 207–241. doi:10.1002/ange.19720840843. https://archive.org/details/chemistryofacety0000vieh ↩

  9. 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. /wiki/Melville_Wolfrom ↩

  10. 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. 9780471720911 ↩