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Nef synthesis

From Wikipedia, the free encyclopedia
Not to be confused withNef isocyanide reaction orNef reaction.
Nef synthesis
Named afterJohn Ulric Nef
Reaction typeCoupling reaction
Identifiers
RSC ontology IDRXNO:0000506

Inorganic chemistry,Nef synthesis is the addition of sodiumacetylides toaldehydes andketones to yieldpropargyl alcohols.[1][2][3][4][5][6] It is named forJohn Ulric Nef, who discovered the reaction in 1899.

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

See also

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References

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  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. Retrieved25 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. ^abOroshnik, 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. Retrieved25 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. Retrieved24 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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