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The reaction has been the subject of several literature reviews. [1] [2] [3] The Nef reaction: 1. Salt of a nitroalkane 3. Ketone 4. Nitrous oxide. 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% ...
These alkoxy radicals are susceptible to C—C fragmentation reactions, which explains the formation of a mixture of products. [5] Alternatively, nitroethane can be produced by the Victor Meyer reaction of haloethanes such as chloroethane, bromoethane, or iodoethane with silver nitrite in diethyl ether or THF.
The aza-Henry reaction is also used to produce nitroamines and can be a reliable synthetic route for the synthesis of vicinal diamines. [13] Perhaps one of the most synthetically useful modifications to the Henry reaction is the use of an organocatalyst. [2] [12] [14] The catalytic cycle is shown below. Henry reaction synthetic scheme
In the so-called Ter Meer reaction (1876) named after Edmund ter Meer, [14] the reactant is a 1,1-halonitroalkane: The reaction mechanism is proposed in which in the first slow step a proton is abstracted from nitroalkane 1 to a carbanion 2 followed by protonation to an aci-nitro 3 and finally nucleophilic displacement of chlorine based on an ...
Nitromethane reacts with solutions of sodium hydroxide or methoxide in alcohol to produce an insoluble salt of nitromethane. This substance is a sensitive explosive which reverts to nitromethane under acidic conditions and decomposes in water to form another explosive compound, sodium methazonate, which has a reddish-brown color:
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The reaction utilizes benzene as a solvent and proceeds to about 90% yield in 12 hours. [9] Reaction of nitroethylene and aniline. Another example of nitroethylene is from the coupling reaction with a vinyl Grignard reagent and a silyl glyoxalate to form a nitrocylopentanol. This process via a Henry reaction and is highly diastereoselective. [10]
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