- Ionic-Liquid Controlled Nitration of Double Bond: Highly Selective Synthesis of Nitrostyrenes and Benzonitriles
-
Unprecedented in literature, the conversion of aryl alkenes into β-nitrostyrenes (2) or benzonitriles (3) with sodium nitrite can be governed by an appropriate choice of ionic liquid (IL) medium. A general trend was found for the selectivity of these processes, which depends on the nature of IL, with imidazolium-based ILs, such as [Bmim]Cl, that favor the C–H nitration leading to β-nitrostyrenes, while tetraalkylammonium-based ILs, such as TBAA, privilege the C=C bond cleavage affording benzonitriles. Besides a substrate scope, mechanistic hypotheses were provided on the origin of the different selectivity in the two kinds of ILs, based on their own tunable properties such as polarity, viscosity, and solvent cage effects.
- Casiello, Michele,Caputo, Daniela,Fusco, Caterina,Cotugno, Pietro,Rizzi, Vito,Dell'Anna, Maria Michela,D'Accolti, Lucia,Nacci, Angelo
-
-
Read Online
- In order to iodide is one pot synthesis nitryl source α, β - unsaturated nitro olefin derivatives (by machine translation)
-
The present invention discloses a one-pot synthesis nitryl source iodide is α, β - unsaturated nitro olefin derivatives, vinyl compounds containing four aryl ferrous (III), iodide and tertiary-butyl hydrogen peroxide in acetonitrile solution system a pot of reaction, generating α, β - unsaturated nitro olefin derivatives; the method to achieve the under mild reaction conditions, high yield with high stereo selectivity of the E synthesis of α, β - unsaturated nitro olefin. (by machine translation)
- -
-
Paragraph 0055-0058; 0110-0112
(2017/09/01)
-
- Α, β - unsaturated nitro olefin derivative synthesis method (by machine translation)
-
The invention discloses a α, β - unsaturated nitro olefin derivative synthesis method, vinyl compounds containing four aryl ferrous (III), ammonium halide and tertiary-butyl hydrogen peroxide in the system of the one-pot reaction, generating α, β - unsaturated nitro olefin derivatives; the method to achieve the under mild reaction conditions, high yield with high stereo selectivity of the E synthesis of α, β - unsaturated nitro olefin. (by machine translation)
- -
-
Paragraph 0027; 0034; 0057; 0059; 0111; 0112; 0113
(2017/09/05)
-
- Stereoselective nitration of olefins with tBuONO and TEMPO: Direct access to nitroolefins under metal-free conditions
-
Nitroolefins are essential elements for both synthetic chemistry and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.
- Maity, Soham,Naveen, Togati,Sharma, Upendra,Maiti, Debabrata
-
supporting information
p. 3384 - 3387
(2013/07/26)
-
- Synthesis of (E)-nitroalkenes catalysed by ethanolamine supported on silica
-
A simple method for preparing (E)-nitroalkenes based on a Henry reaction in the presence of a heterogenized homogeneous catalyst consisting of silica-supported ethanolamine is proposed. With 4-substituted benzaldehydes, the reaction gives the corresponding (E)-nitrostyrenes in high yields and a short time. Heterocyclic carboxaldehydes also give good results, but the presence of an N or S atom in the ring has a slightly adverse effect on the reaction. The synthetic process is quite novel and interesting. The catalyst remains active and exhibits no substantial loss of activity or selectivity over up to three reaction cycles.
- Mora, Manuel,Jimenez-Sanchidrian, Cesar,Urbano, Francisco Jose,Ruiz, Jose Rafael
-
experimental part
p. 131 - 137
(2010/11/03)
-
- A straightforward and efficiently scaleable synthesis of novel racemic 4-substituted-2,8-diazaspiro[4.5]decan-1-one derivatives
-
Novel and straightforward syntheses (3-5 steps, high yields) of racemic diazaspiropiperidine derivatives based on the Michael addition of pipecolate-derived enolates to a range of nitroalkenes have been developed. The reaction has been shown to have a gen
- Krafft, Eva A.,Kurt, Anke,Maier, Axel,Thomas, Andrew W.,Zimmerli, Daniel
-
p. 3245 - 3252
(2007/10/03)
-
- Synthese d'aryl nitronorbornenes par cycloaddition de Diels-Alder entre les aryl-nitroethylenes et le cyclopentadiene. Justification de la stereochimie et de la reactivite relative observees par la methode CNDO/II. Obtention d'aryl aminonorbornenes
-
Syntheses of numerous 2-aryl nitroethylenes (nitrostyrenes) have been optimized.The nitrostyrenes have been reacted with cyclopentadiene in Diels-Alder cycloadditions and the 3-aryl 2-nitronorbornenes obtained have been reduced into 3-aryl 2-aminonorbornenes.These compounds are potentially dopaminergic molecules.The stereochemistry of the adducts obtained in the Diels-Alder reaction has been determined by 1H nmr.The stereochemistry and the relative reactivity of the nitrostyrenes versus cyclopentadiene have been confirmed by theoretical calculations based on the CNDO/II method.
- Bourguignon, Jean,Le Nard, Gilles,Queguiner, Guy
-
p. 2354 - 2361
(2007/10/02)
-