Nef synthesis

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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.

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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

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.
  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)
  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. Bibcode:1947JAChS..69..239H. doi:10.1021/ja01194a018.
  4. 1 2 Oroshnik, William; Mebane, Alexander D. (1949). "The Nef Reaction with α,β-Unsaturated Ketones". Journal of the American Chemical Society. 71 (6): 2062–2065. Bibcode:1949JAChS..71.2062O. 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.


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