Chemistry:Nef synthesis
From HandWiki
| 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
- Favorskii reaction
- Alkynation
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. https://zenodo.org/record/1427517.
- ↑ Johnson, A. W. (1946). The Chemistry of the Acetylenic Compounds (1st ed.). London: Arnold. p. 11. ISBN 978-0-598-99095-2. https://books.google.com/books?id=e7E3AAAAMAAJ. Retrieved 25 February 2016.
- ↑ 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. Bibcode: 1947JAChS..69..239H.
- ↑ 4.0 4.1 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. Bibcode: 1949JAChS..71.2062O.
- ↑ Raphael, Ralph Alexander (1955). Acetylenic Compounds in Organic Synthesis (1st ed.). London: Butterworths. p. 10. http://babel.hathitrust.org/cgi/pt?id=mdp.39015064396958;view=1up;seq=1. 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. https://archive.org/details/chemistryofacety0000vieh.
- ↑ Wolfrom, Melville L. (1960). "John Ulric Nef: 1862—1915". Biographical Memoirs (1st ed.). Washington, DC: National Academy of Sciences. p. 218. http://www.nasonline.org/publications/biographical-memoirs/memoir-pdfs/nef-john-u.pdf. 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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