- Synthesis and Tautomerization of 2-Nitro-1-nitrosoethylbenzene in Acetone
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2-Nitro-1-nitrosoethylbenzene has been synthesized in fairly high yield and its tautomerization studied by 1H NMR spectroscopy.
- Shaabani, Ahmad,Ameri, Majid,Bijanzadeh, Hamid Reza
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- Synthesis of α-Nitro Ketoximes from Styrenes and tert-Butyl Nitrite
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We have discovered that various α-nitro ketoximes can be synthesized in good yields starting from styrenes and tert-butyl nitrite. The success of the reaction was critically dependent on the use of a mixture solvent of dimethylsulfoxide and water. The reaction can tolerate a wide variety of substituents including electron-withdrawing and electron-donating groups.
- Cao, Qi,Liu, Jidan,Yu, Lin,Gui, Qingwen,Chen, Xiang,Tan, Ze
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- AgNO3as Nitrogen Source for Cu-Catalyzed Cyclization of Oximes with Isocyanates: A Facile Route to N-2-Aryl-1,2,3-triazoles
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A versatile copper-catalyzed [3 + 1 + 1] annulation of oximes and isocyanates with AgNO3 is described. In this conversion, AgNO3 and isocyanates instead of conventional azide or diazonium reagents were used as the nitrogen source. This three-component transformation was achieved by cleaving N-O/C-H/C-N bonds and building CN/N-N bonds, which provides a strategy to prepare N-2-aryl-1,2,3-triazoles with a good substrate and functional compatibility.
- Liang, Jingwen,Rao, Yingqi,Zhu, Weidong,Wen, Tingting,Huang, Junjie,Chen, Zhichao,Chen, Lu,Li, Yibiao,Chen, Xiuwen,Zhu, Zhongzhi
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supporting information
p. 7028 - 7032
(2021/09/14)
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- Ionic-Liquid Controlled Nitration of Double Bond: Highly Selective Synthesis of Nitrostyrenes and Benzonitriles
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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
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supporting information
p. 6012 - 6018
(2020/08/24)
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- Water-controlled nitro-oximation of alkenes under catalyst-free conditions
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A convenient and precise nitration and oximation of alkenes with tert-butyl nitrite has been reported, yielding α-nitro ketoximes in satisfactory yields with broad substrate generality and excellent stereoselectivity under mild conditions. Experiments indicate that tert-butyl nitrite serves as both NO and NO2 sources and water plays a key role in this difunctionalization reaction.
- Tang, Lin,Yang, Zhen,Chang, Xueping,Zou, Guodong,Zhou, Yuqiang,Rao, Weihao,Ma, Xiantao,Zhao, Geng
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p. 4272 - 4275
(2018/10/31)
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- Preparation method of alpha-nitro ketoxime derivative
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The invention belongs to the field of organic synthesis, and specifically discloses a preparation method of alpha-nitro ketoxime derivatives. The method comprises the steps of taking a styrene derivative of the formula I-1 as a reaction raw material and butyl nitrite as a nitration reagent, adding an assistant, and reacting with water as a solvent under the condition of air at room temperature to obtain the alpha-nitro ketoxime derivative of formula I, has the characteristics of low production cost, mild process conditions, high yield, and environmentally friendly effects, and is very suitable for industrial production. The reaction formula of the method is shown in the description.
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Paragraph 0021; 0022
(2018/04/01)
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- Direct synthesis of nitriles from cleavage of C=C double bond with nitrite as the nitrogen source and oxidant
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The transformation of the C=C bond of olefin to nitriles has been developed, using easily available NaNO2 as both the nitrogen source and oxidant. Several aryl, heterocyclic nitriles with various substituting groups could be successfully prepared in good to high yields. Based upon experimental observations, a possible reaction mechanism is proposed.
- Liu, Qiang,Fang, Bao,Bai, Xiaohui,Liu, Yuan,Wu, Yao,Xu, Guiming,Guo, Cancheng
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supporting information
p. 2620 - 2623
(2016/06/01)
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- Nitration-Oximization of Styrene Derivatives with tert-Butyl Nitrite: Synthesis of α-Nitrooximes
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A highly efficient method for direct nitration-oximization of styrene derivatives using tert-butyl nitrite (t-BuONO) in DMSO was developed. The present method offers a convenient and practical approach for the synthesis of α-nitrooximes in moderate to high yields. The salient features entail mild reaction conditions, metal-free reagent, environmentally benign solvent and simple experimental procedure.
- Chumnanvej, Napasawan,Katrun, Praewpan,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Kuhakarn, Chutima
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p. 830 - 838
(2016/09/03)
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- Convenient synthesis of α-nitrooximes mediated by OXONE
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A novel OXONE mediated direct difunctionalization of alkenes with NaNO2 in aqueous acetonitrile for the synthesis of α-nitrooximes was developed. The α-nitrooximes were readily prepared in moderate to high yields at room temperature under mild reaction conditions. The present protocol offers an easy and environmentally benign approach to access various α-nitrooximes derived from styrene derivatives.
- Chumnanvej, Napasawan,Samakkanad, Natthapol,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
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p. 59726 - 59732
(2015/02/19)
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- Synthesis and tautomerization study of pseudonitrosites to 1,2-nitroximes
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4-R-Substituted 2-nitro-1-nitrosoethylbenzenes (R = H, CH3, OCH3, Cl, F) have been synthesized under solvent-free conditions and the mechanism of their tautomerization to 2-isonitroso-1-nitro-2-phenylethanes have been investigated by 1H NMR spectroscopy.
- Shaabani, Ahmad,Bijanzadeh, Hamid Reza,Karimi, Ali Reza,Teimouri, Mohammad Bagher,Soleimani, Kamal
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p. 248 - 252
(2008/09/19)
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- The chemistry of peroxynitrite: Involvement of an ET process in the radical nitration of unsaturated and aromatic systems
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Reactions of peroxynitrous acid, HPN, with styrene under acidic conditions lead to the oxime 1, the nitrate 2, benzaldehyde (3), and α-nitroacetophenone (4) in overall yields that depend strongly on the pH value and with a product distribution that depends on the dioxygen concentration. The results are rationalized by assuming that HPN undergoes acid-catalyzed decomposition to give nitrous anhydride, or its synthetic equivalent, which is responsible for the regioselective nitration of the styrene double bond by an ET process. The resulting β-nitrobenzyl radical 6 can, depending on the reaction conditions, undergo reversible coupling with nitric oxide to afford the nitroso derivative 7 and then the tautomeric oxime 1, or trapping by dioxygen, eventually leading to products 2, 3, and 4 through the intermediacy of the peroxynitrite derivative 8. Oxime 1 and nitrate 2 are also obtained by treating styrene with nitrous anhydride under protic conditions, the latter being produced in situ from nitric oxide/dioxygen. Similarly to styrene, 1,4-diphenylbutadiene (14) gives radicals 22 and 21 by competitive trapping at the side chain and at the aromatic ring. In turn, radicals 22 and 21 undergo β-fragmentation reactions or trapping by dioxygen with eventual formation of nitrates 16 and 17, cinnamic aldehyde (18), and the diol 15. Finally, the HPN-promoted reaction of p-cresol (27) leads to the 2-nitro derivative 28 through an initial electron-transfer process followed by in cage recombination of the resulting radical ion pair.
- Grossi, Loris,Montevecchi, Pier Carlo,Strazzari, Samantha
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p. 741 - 748
(2007/10/03)
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- New NO-donors with antithrombotic and vasodilating activities, Part 21. Pseudonitrosites and other azodioxides with vicinal electron acceptors.
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Twelve vicinally substituted nitro-nitroso compounds (pseudonitrosites) were synthesized, nine of them for the first time. In the solid state the dimeric azodioxides are present. In the class of the pseudonitrosites 2a-h, all compounds exhibited comparatively strong antiplatelet activity in vitro (Born test, collagen). Four of them showed an IC50 below 10 microM, 2a being the most active substance with an IC50 = 2.1 microM. When administered orally to rats (60 mg/kg) small antithrombotic effects were observed. The pseudonitrosite 6d was the most active compound (18% inhibition in arterioles). The in vitro decomposition of 2a at 37 degrees C gave NO and N2O, indicating that the above pharmacological effects were mediated by an NO-dependent mechanism. The replacement of the nitro group in the pseudonitrosite partial structure by other electron acceptors i.e. acetyl, carboxyl, or acetyloxy groups leads to inactive (10a) or less active compounds (10b, e).
- Rehse,Herpel
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p. 111 - 117
(2007/10/03)
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- Investigation of the Potential of Molybdenum(VI) Hydrazido(2-) Complexes as Sources of Nitrenium Ions: Cleavage of the N-N Bond and Incorporation of the β-Nitrogen Group into Solvent Molecules
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Photolyis or thermolysis of bis(N,N-dimethyldithiocarbamato)bismolybdenum(VI) complexes in 1,1,2,2-tetrachloroethane results predominantly in transfer of the hydrazido group to the solvent with formation of dichloroacetohydrazides.A small amount of the corresponding dichloroacetamides are produced by N-N cleavage and N(R)Ph transfer.In contrast, the latter process dominates the reaction of dichlorobis(N,N-dimethyldithiocarbamato)mono-molybdenum(VI) complexes with silver nitrate in alcohols occuring concomitantly with ring methoxylation and nitration and N-nitrosation.Neither transfer of N(R)Ph appears to involve free nitrenium ions.
- Baum, Marc M.,Smith, Edward H.
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p. 2513 - 2520
(2007/10/02)
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