Chemical reaction; acid hydrolysis of a nitroalkane salt to a ketone
Not to be confused with Nef isocyanide reaction or Nef synthesis.
Nef reaction
Named after
John Ulric Nef
Reaction type
Substitution reaction
Identifiers
Organic Chemistry Portal
nef-reaction
RSC ontology ID
RXNO:0000157
In organic chemistry, the Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane (R−NO2) to an aldehyde (R−CH=O) or a ketone (R2C=O) and nitrous oxide (N2O). The reaction has been the subject of several literature reviews.[1][2][3]
The reaction was reported in 1894 by the chemist John Ulric Nef,[4] who treated the sodium salt of nitroethane with sulfuric acid resulting in an 85–89% yield of nitrous oxide and at least 70% yield of acetaldehyde. However, the reaction was pioneered a year earlier in 1893 by Konovalov,[5] who converted the potassium salt of 1-phenylnitroethane with sulfuric acid to acetophenone.
^Noland, Wayland E. (1955). "The NEF Reaction". Chemical Reviews. 55 (1): 137–155. doi:10.1021/cr50001a003.
^Pinnick, Harold W. (1990). "The Nef Reaction". In Paquette, Leo A. (ed.). Organic Reactions Volume 38 (1st ed.). New York: Wiley. pp. 655–792. doi:10.1002/0471264180.or038.03. ISBN 9780471515944.
^Grierson, David S.; Husson, Henri-Philippe (1991). "4.7 – Polonovski- and Pummerer-type Reactions and the Nef Reaction". In Trost, Barry; Fleming, Ian (eds.). Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Synthesis, Volume 6 (1st ed.). New York: Pergamon. pp. 909–947. doi:10.1016/B978-0-08-052349-1.00175-X. ISBN 9780080359298.
^Nef, John Ulric (1894). "Ueber die Constitution der Salze der Nitroparaffine". Justus Liebigs Annalen der Chemie. 280 (2–3): 263–291. doi:10.1002/jlac.18942800209.
^Konovalov.,: J. Russ. Phys. Chem. Soc. 2 1893, 6(I), 509.
In organic chemistry, the Nefreaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane (R−NO2) to...
The Nef isocyanide reaction is an addition reaction that takes place between isocyanides and acyl chlorides to form imidoyl chloride products, a process...
as a Michael acceptor. Nitronates are also key intermediates in the Nefreaction: when exposed to acids or oxidants, a nitronate hydrolyzes to a carbonyl...
cyclization, cyclic ketones are prepared from dicarboxylic acids. In the Nefreaction, ketones form by hydrolysis of salts of secondary nitro compounds. In...
carbon dioxide. Aldehydes participate in many reactions. From the industrial perspective, important reactions are: condensations, e.g., to prepare plasticizers...
John Ulric Nef, who discovered the reaction in 1899. This process is often erroneously referred to as the Nefreaction, which is an unrelated chemical transformation...
Sometimes this reaction is erroneously called the Nefreaction, a name more often used to describe a different reaction (see Nefreaction). Chemist Walter...
DMDO can also be used to convert nitro compounds to carbonyl compounds (Nefreaction). Difluorodioxirane Dioxirane Shi epoxidation "Robert W. Murray Biography"...
Nitronates are formed as intermediates in the Henry reaction, Hass–Bender oxidation and Nefreaction, the latter of which also demonstrates the instability...
provides an alternative to the Nefreaction; for example, for ketomacrolide synthesis where complicating side reactions usually encountered using other...
hydroxamic acids, although yields are only about 50%. In a variation on the Nefreaction, primary nitro compounds kept in an acidic solution (to minimize the...
hydroxide and then to the shortened aldose by reaction with Iron(III) sulfate and hydrogen peroxide. Nefreaction Wohl, A. (1893), "Abbau des Traubenzuckers"...
discovers diethylzinc 1890 Ludwig Mond discovers nickel carbonyl 1899 John Ulric Nef discovers alkynylation using sodium acetylides. 1909 Paul Ehrlich introduces...
nitroalkanes, leads to carbonyl compounds in an example of an oxidative Nefreaction. (9) Sulfide oxidation in the presence of a single equivalent of DMD...
physicist David S. Moore – statistician John Ulric Nef – chemist who discovered the Nefreaction Ei-ichi Negishi – Professor of Chemistry, Nobel Laureate...
Nef synthesis, a chemical reaction whereby a chiral propargyl alcohol is prepared from a terminal alkyne and an aldehyde. This alkynylation reaction is...
mother Mark Blum as Mr. Mooney, the owner of Mooney's and Joe's boss Hari Nef as Blythe, a rival graduate student to Beck John Stamos as Dr. Nicky, Beck's...
of the nef gene that is present in most SIVs. For non-pathogenic SIV variants, nef suppresses T cell activation through the CD3 marker. Nef's function...
Barthélemy, L. (1883) "La savonnerie marseillaise", noted by Nef 1936:660 note 99. Nef 1936:653, 660. Keith Thomas, 'Noisomeness,' London Review of Books...
undergo insertion into the C–Cl bonds of acyl chlorides in the Nef isocyanide reaction, a process that is believed to be concerted and illustrates their...
C6H5Na is an organosodium compound. Solid phenylsodium was first isolated by Nef in 1903. Although the behavior of phenylsodium and phenyl magnesium bromide...