Nef synthesis

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.

References

^ 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.
^ 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)
^ 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.
^ ^a ^b 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.
^ Raphael, Ralph Alexander (1955). Acetylenic Compounds in Organic Synthesis (1st ed.). London: Butterworths. p. 10. Retrieved 25 February 2016.
^ Coffman, Donald D. (1940). "Dimethylethhynylcarbinol". Organic Syntheses. 40: 20. doi:10.15227/orgsyn.020.0040.
^ Viehe, Heinz Günter (1969). Chemistry of Acetylenes (1st ed.). New York: Marcel Dekker, inc. pp. 207–241. doi:10.1002/ange.19720840843.
^ 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.
^ 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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[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.

[Oroshnik-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. 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.

[Viehe-7] Viehe, Heinz Günter (1969). Chemistry of Acetylenes (1st ed.). New York: Marcel Dekker, inc. pp. 207–241. doi:10.1002/ange.19720840843.

[Wolfrom-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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Nef synthesis

Nef synthesis

Nef synthesis

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