3457-58-7Relevant academic research and scientific papers
Metal-Free C-Arylation of Nitro Compounds with Diaryliodonium Salts
Dey, Chandan,Lindstedt, Erik,Olofsson, Berit
, p. 4554 - 4557 (2015/09/28)
An efficient, mild, and metal-free arylation of nitroalkanes with diaryliodonium salts has been developed, giving easy access to tertiary nitro compounds. The reaction proceeds in high yields without the need for excess reagents and can be extended to α-arylation of nitroesters. Nitroalkanes were selectively C-arylated in the presence of other easily arylated functional groups, such as phenols and aliphatic alcohols.
NITRATED HYDROCARBONS, DERIVATIVES, AND PROCESSES FOR THEIR MANUFACTURE
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Page/Page column 30-31; 33, (2009/12/02)
Provided is a process for the formation of nitrated compounds by the nitration of hydrocarbon compounds with dilute nitric acid. Also provided are processes for preparing industrially useful downstream derivatives of the nitrated compounds, as well as novel nitrated compounds and derivatives, and methods of using the derivatives in various applications.
An efficient nitration of light alkanes and the alkyl side-chain of aromatic compounds with nitrogen dioxide and nitric acid catalyzed by N-hydroxyphthalimide
Nishiwaki, Yoshiki,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 5663 - 5668 (2007/10/03)
Nitration of light alkanes and the alkyl side-chain of aromatic compounds with NO2 and HNO3 was successfully achieved by the use of N-hydroxyphthalimide (NHPI) as a catalyst under relatively mild conditions. For example, the nitration of propane with NO2 catalyzed by NHPI at 100 °C for 14 h gave 2-nitropropane in good yield without formation of 1-nitropropane and cleaved products such as nitroethane and nitromethane. Various aliphatic nitroalkanes, which are difficult to prepare by conventional methods, could be selectively obtained by means of the present methodology by using NHPI as the key catalyst. In addition, the side-chain nitration of alkylbenzenes such as toluene was selectively carried out to lead to α-nitrotoluene without the ring nitration. The present reaction provides an efficient selective method for the nitration of light alkanes and alkylbenzenes, which has been very difficult to carry out so far.
Intramolecular Nucleophilic Substitution on Nitrogen A New Heterocyclic Synthesis
Sheradsky, Tuvia,Yusupova, Larissa
, p. 7701 - 7704 (2007/10/02)
A series of 5-(diphenylphosphinyloxyamino)valeric acid esters has been prepared.Their treatment with appropriate bases led to cyclization to proline derivatives.The reaction constitutes the first reported case of intramolecular nucleophilic substitution o
Mechanisms in the reaction of arenediazonium cations with 2-nitropropanide anion
Khanna, Rajive K.,Jiang, Yong M.,Singh
, p. 5449 - 5452 (2007/10/02)
Lithium 2-nitropropan-2-ide reacts, in MeOH solvent, with benzenediazonium and p-methoxybenzenediazonium cations to give diazo-coupled products, but with p-nitrobenzenediazonium cation by competing electron transfer and diazo-coupling reactions.
Electron-Transfer Substitution Reactions: Facilitation by the Cyano Group
Kornblum, Nathan,Fifolt, Michael J.
, p. 1311 - 1322 (2007/10/02)
It is now clear that a cyano group facilitates electron-transfer substitution reactions.Of particular interest is the demonstration that electron-transfer chain substitution at a saturated carbon atom has been achieved in the absence of a nitro group.
The Chemistry of Pentavalent Organobismuth Reagents. Part 7. The Possible Role of Radical Mechanisms in the Phenylation Process for Bismuth(V), and Related Lead(IV), Iodine(III), and Antimony(V) Reagents
Barton, Derek H. R.,Finet, Jean-Pierre,Giannotti, Charles,Halley, Frank
, p. 241 - 250 (2007/10/02)
The phenylation reactions of bismuth(V), lead(IV), and iodine(III) have been examined to test the presence or absence of phenyl radicals.In the case of several bismuth(V) reactions the presence of phenyl radicals has been detected, but it has been shown, by use of a large excess of radical trapping agent, that these radicals have nothing to do with the phenylation process.In the same way, the other phenylation reactions fail to respond to a large excess of a radical trap.
Arylation with Aryllead Triacetates Produced in situ by Mercury-Lead Exchange
Kozyrod, Robert P.,Pinhey, John T.
, p. 1155 - 1161 (2007/10/02)
The addition of lead tetraacetate to diphenylmercury in chloroform leads to the rapid formation of a solution of phenyllead triacetate, which has been used directly for the C-phenylation of ethyl 2-oxocyclopentanecarboxylate (1) and 2-nitropropane in good
Pentavalent Organobismuth Reagents. Part 3. Phenylation of Enols and of Enolate and other Anions
Barton, Derek H. R.,Blazejewski, Jean-Claude,Charpiot, Brigitte,Finet, Jean-Pierre,Motherwell, William B.,et al.
, p. 2667 - 2676 (2007/10/02)
The phenylation of enols and of enolate anions of ketones, β-diketones and keto esters has been studied using a range of Bi reagents.Under basic conditions C-phenylation is observed and, even hindered, perphenylated compounds are easily synthesized.Under neutral and acidic conditions ordinary ketones do not react and enolic systems give O-phenylation.A number of other anions have been phenylated under basic conditions, including the key compound indole wich mainly gave 3-C-phenylation.All these reactions can be supposed to have one of two alternative mechanisms, which parallel the two mechanisms proposed for the phenylation of phenols.
The Chemistry of Aryllead(IV) Tricarboxylates. The C-Arylation of Nitroalkanes and Nitronate Salts with Aryllead Triacetates
Kozyrod, Robert P.,Pinhey, John T.
, p. 713 - 721 (2007/10/02)
2-Nitropropane reacts with phenyllead triacetate in dimethyl sulfoxide to give 2-nitro-2-phenylpropane in good yield.This arylation of nitroalkanes has been examined with a variety of substrates and a number of aryllead triacetates, and in those cases where there was no steric hindrance the reaction was found to be quite general.Reactions of nitroethane and methyl nitroacetate, compounds with two α-hydrogens, were readily controlled to give either the mono- or di-arylated products.The corresponding nitronate salts were also examined and found to undergo the arylation reaction in similar yield but at a very much faster rate.
