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Journal articles on the topic 'Nitroalkanes'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 June 2025

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1

Chen, Ren Er, Yan Li Wang, Zhi Wei Chen, and Wei Ke Su. "A novel and efficient synthesis of bis(benzofuranyl)methanes and 2-benzofuran-1-nitroalkanes catalyzed by Bi(OTf)." Canadian Journal of Chemistry 86, no. 9 (2008): 875–80. http://dx.doi.org/10.1139/v08-091.

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Bismuth (III) triflate-catalyzed Friedel-Crafts reactions between benzofuran and aldehydes in different solvents were investigated. Bis(benzofuranyl)methanes were obtained with good yields when acetonitrile was used as solvent, while in the case of nitromethane the multi-component reaction products, 2-benzofuran-1-nitroalkanes, were formed under similar conditions. A plausible mechanism is given.Key words: benzofuran, aldehyde, bis(benzofuranyl)methanes, Bi(OTf)3, 2-benzofuran-1-nitroalkane.

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2

Kuo, C. F., and I. Fridovich. "Free-radical chain oxidation of 2-nitropropane initiated and propagated by superoxide." Biochemical Journal 237, no. 2 (1986): 505–10. http://dx.doi.org/10.1042/bj2370505.

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The superoxide radical O2.-, whether produced by the xanthine/xanthine oxidase reaction or infused as KO2, solubilized by a crown ether in dry dimethyl sulphoxide, initiated a free-radical chain oxidation of anionic 2-nitropropane. Superoxide dismutase, but not catalase, inhibited oxidation of the nitroalkane. Xanthine oxidase suffered a syncatalytic inactivation, during the co-oxidation of 2-nitropropane, which was reversed by dialysis. Cyanide exacerbated this syncatalytic inactivation and rendered it irreversible. The frequently observed oxidations of nitroalkanes by flavoenzymes now need to be re-examined to clarify the extent to which O2.--initiated free-radical chain oxidation contributed to the overall nitroalkane oxidation.

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3

Zheng, Peng-Fei, Yang An, Zuo-Yi Jiao, Zhou-Bao Shi та Fu-Min Zhang. "Comprehension of the α-Arylation of Nitroalkanes". Current Organic Chemistry 23, № 14 (2019): 1560–80. http://dx.doi.org/10.2174/1385272823666190820113718.

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Background: α-Aryl substituted nitroalkanes are important synthetic intermediates for the preparation of pharmaceutical molecules, natural products, and functional materials. Due to their scare existence in Nature, synthesis of these compounds has attracted the attention of synthetic and medicinal chemists, rendering α-arylation of nitroalkanes of an important research topic. This article summarizes the important advances of α- arylation of nitroalkanes since 1963. Results: After a brief introduction of the synthetic application and the reactions of nitroalkanes, this article reviewed the synthetic methods for the α-arylated aliphatic nitro compound. The amount of research on α-arylation of nitroalkanes using various arylation reagents and the discovery of elegant synthetic approaches towards such skeleton have been discussed. This review described these advances in two sections. One is the arylation of non-activated nitroalkanes, with an emphasis on the application of diverse arylation reagents; the other focuses on the arylation of activated nitroalkanes, including dinitroalkanes, trinitroalkanes, α-nitrosulfones, α-nitroesters, α-nitrotoluenes, and α-nitroketones. The synthetic application of these methods has also been presented in some cases. Conclusion: In this review, we described the progress of α-arylation of nitroalkanes. Although the immense amount of research on α-arylation of aliphatic nitro compounds has been achieved, many potential issues still need to be addressed, especially the asymmetric transformation and its wide application in organic synthesis.

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4

Gorlatova, Natalia, Marek Tchorzewski, Tatsuo Kurihara, Kenji Soda, and Nobuyoshi Esaki. "Purification, Characterization, and Mechanism of a Flavin Mononucleotide-Dependent 2-Nitropropane Dioxygenase fromNeurospora crassa." Applied and Environmental Microbiology 64, no. 3 (1998): 1029–33. http://dx.doi.org/10.1128/aem.64.3.1029-1033.1998.

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ABSTRACT A nitroalkane-oxidizing enzyme was purified to homogeneity fromNeurospora crassa. The enzyme is composed of two subunits; the molecular weight of each subunit is approximately 40,000. The enzyme catalyzes the oxidation of nitroalkanes to produce the corresponding carbonyl compounds. It acts on 2-nitropropane better than on nitroethane and 1-nitropropane, and anionic forms of nitroalkanes are much better substrates than are neutral forms. The enzyme does not act on aromatic compounds. When the enzyme reaction was conducted in an18O2 atmosphere with the anionic form of 2-nitropropane as the substrate, acetone (with a molecular mass of 60 Da) was produced. This indicates that the oxygen atom of acetone was derived from molecular oxygen, not from water; hence, the enzyme is an oxygenase. The reaction stoichiometry was 2CH3CH(NO2)-CH3 + O2→2CH3COCH3 + 2HNO2, which is identical to that of the reaction of 2-nitropropane dioxygenase from Hansenula mrakii. The reaction of theNeurospora enzyme was inhibited by superoxide anion scavengers in the same manner as that of the Hansenulaenzyme. Both of these enzymes are flavoenzymes; however, theNeurospora enzyme contains flavin mononucleotide as a prosthetic group, whereas the Hansenula enzyme contains flavin adenine dinucleotide.

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5

Karthikeyan, K., R. Senthil Kumar, P. Dheenkumar, and Paramasivan T. Perumal. "Solvent and catalyst free route to 3-indolyl glycoconjugates: synthesis of sugar tethered isoxazolines and isoxazoles from 3-indolyl nitroalkanes." RSC Adv. 4, no. 53 (2014): 27988–97. http://dx.doi.org/10.1039/c4ra02825b.

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An expedient, solvent and catalyst free strategy for the synthesis of sugar based bis(indolyl)methanes and indolyl nitroalkanes has been developed. Further, the nitroalkanes were converted to novel isoxazolines and isoxazoles by nitrile oxides cycloaddition.

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6

Smith, David J., and Robin C. Anderson. "Toxicity and Metabolism of Nitroalkanes and Substituted Nitroalkanes." Journal of Agricultural and Food Chemistry 61, no. 4 (2013): 763–79. http://dx.doi.org/10.1021/jf3039583.

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7

González, Patricia Camarero, Sergio Rossi, Miguel Sanz, Francesca Vasile, and Maurizio Benaglia. "Synthesis of Tetrasubstituted Nitroalkenes and Preliminary Studies of Their Enantioselective Organocatalytic Reduction." Molecules 28, no. 7 (2023): 3156. http://dx.doi.org/10.3390/molecules28073156.

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Starting from commercially available ketones, a reproducible and reliable strategy for the synthesis of tetrasubstituted nitroalkenes was successfully developed, using a two-step procedure; the HWE olefination of the ketone to form the corresponding α,β-unsaturated esters is followed by a nitration reaction to introduce the nitro group in the α position of the ester group. The enantioselective organocatalytic reduction of these compounds has also been preliminarily studied, to access the functionalized enantioenriched nitroalkanes, which are useful starting materials for further synthetic elaborations. The absolute configuration of the reduction product was established by chemical correlation of the chiral nitroalkane with a known product; preliminary DFT calculations were also conducted to rationalize the stereochemical outcome of the organocatalytic enantioselective reduction.

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8

Gisya, Abdi, and Alizadeh Abdolhamid. "Surface-induced formation of stereogenic centers on gold nanoparticles through diastereoselective interfacial Henry reaction: an NMR investigation." Gold Bulletin 51 (June 6, 2018): 65–74. https://doi.org/10.1007/s13404-018-0232-5.

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This study aims at the synthesis of gold nanoparticles (2–3 nm) functionalized with different nitroalkane-terminated thiols and investigates the chemical reactivity of these confined nitroalkanes towards aldehydes to yield β-nitroalcohols. Interfacial Henry reaction between fixed nitroalkane-terminated thiols with various aromatic and heteroaromatic aldehydes resulted in stereogenic centers on the surface of mixed-monolayer-protected gold nanoparticles (MMPNs). The ratio of the resulting diastereomers was determined by 1H NMR spectroscopy. It was found that some parameters such as the chain length of nitroalkyl and the nature of aromatic aldehyde play the main role in affecting the diastereomeric ratio on the surface of MMPNs. Certain trends have been analyzed from the data, and it can be inferred that some aldehydes approximately prefer the formation of anti diastereomers as the predominant products, while others give syn β-nitroalcohols. We have attributed this stereoselectivity to the packed layers, forceful lateral interactions (van derWaals), and intramolecular hydrogen bonding on the surface of modified gold nanoparticles that are able to suppress the role of solvent and intermolecular interactions.

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9

Otevrel, Jan, David Svestka, and Pavel Bobal. "Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones." Organic & Biomolecular Chemistry 17, no. 21 (2019): 5244–48. http://dx.doi.org/10.1039/c9ob00884e.

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10

Cui, Dong-Xiao, Yue-Dan Li, Jun-Chao Zhu, Yan-Yan Jia, Ai-Dong Wen, and Ping-An Wang. "Highly Efficient Michael Reactions of Nitroolefins by Grinding Means." Current Organic Synthesis 16, no. 3 (2019): 449–57. http://dx.doi.org/10.2174/1570179416666190101122150.

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Aim and Objective: The direct β-functionalization of trans-β-nitroolefins by Michael reaction is regarded as an efficient way to provide precursors for β-functional amines. However, Michael additions by grinding means with solvent-free conditons are rarely reported. We have developed facile access to β-functional nitroalkanes by grinding means under solvent-free conditions. Materials and Methods: From commercially available materials including ethyl 2-nitroacetate, alkyl 2-cyanoacetates and malononitrile, the grinding reactions between these above-mentioned activated methylenecompounds and various trans-β-nitroolefins were performed at room temperature and solvent-free conditions. Results: A highly efficient direct Michael reaction of nitroolefins by simple grinding means has been developed. Various trans-nitrostyrenes were easily converted into corresponding β-functional nitroalkanes in excellent yields within 5~10 min (up to 36 examples). Conclusion: Herein, we have developed a simple and efficient way to β-functional nitroalkanes through Michael reactions by grinding means. The grinding Michael reaction is fast, clean and stable and these Michael adducts could be easily converted into the other amino compounds served as building blocks in organic synthesis.

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11

Gietter-Burch, Amber A. S., Vijayarajan Devannah, and Donald A. Watson. "Trifluoromethylation of Secondary Nitroalkanes." Organic Letters 19, no. 11 (2017): 2957–60. http://dx.doi.org/10.1021/acs.orglett.7b01196.

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12

Trost, Barry M, and Jean-Philippe Surivet. "Asymmetric Alkylation of Nitroalkanes." Angewandte Chemie 112, no. 17 (2000): 3252–54. http://dx.doi.org/10.1002/1521-3757(20000901)112:17<3252::aid-ange3252>3.0.co;2-x.

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13

Trost, Barry M, and Jean-Philippe Surivet. "Asymmetric Alkylation of Nitroalkanes." Angewandte Chemie 39, no. 17 (2000): 3122–24. http://dx.doi.org/10.1002/1521-3773(20000901)39:17<3122::aid-anie3122>3.0.co;2-8.

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14

Luk'yanov, O. A., Yu B. Salamonov, A. G. Bass, et al. "Aryl-NNO-azoxy-?-nitroalkanes." Bulletin of the Russian Academy of Sciences Division of Chemical Science 41, no. 10 (1992): 1884–94. http://dx.doi.org/10.1007/bf00863827.

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15

Bai, Zhushuang, Ling Ji, Zemei Ge, Xin Wang, and Runtao Li. "Asymmetric Michael addition reactions of nitroalkanes to 2-furanones catalyzed by bifunctional thiourea catalysts." Organic & Biomolecular Chemistry 13, no. 19 (2015): 5363–66. http://dx.doi.org/10.1039/c5ob00708a.

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16

Tsuchiya, Yuto, Ryota Onai, Daisuke Uraguchi та Takashi Ooi. "Redox-regulated divergence in photocatalytic addition of α-nitro alkyl radicals to styrenes". Chemical Communications 56, № 75 (2020): 11014–17. http://dx.doi.org/10.1039/d0cc04821f.

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17

Bosica, Giovanna, and Ramon Zammit. "One-pot multicomponent nitro-Mannich reaction using a heterogeneous catalyst under solvent-free conditions." PeerJ 6 (June 27, 2018): e5065. http://dx.doi.org/10.7717/peerj.5065.

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An environmentally-friendly, one-pot multicomponent reaction of various aldehydes, amines and nitroalkanes for the synthesis of β-nitroamines is here described. Amberlyst A-21 supported CuI was found to be a highly efficient novel heterogeneous catalyst for the three-component nitro-Mannich reaction between aldehydes, amines and nitroalkanes. The developed protocol is performed in a solvent-free medium to produce a variety of β-nitroamines in good to excellent yields within short reaction times. The catalyst can be easily prepared and recovered. It has been tested up to eight times with only a minor activity loss.

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18

Xu, Dong, Yang Chen, Changmeng Liu, Jiaxi Xu, and Zhanhui Yang. "Iridium-catalyzed highly chemoselective and efficient reduction of nitroalkenes to nitroalkanes in water." Green Chemistry 23, no. 16 (2021): 6050–58. http://dx.doi.org/10.1039/d1gc01907d.

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19

Aksenov, Alexander V., Alexander N. Smirnov, Nicolai A. Aksenov, Asiyat S. Bijieva, Inna V. Aksenova, and Michael Rubin. "Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes." Organic & Biomolecular Chemistry 13, no. 14 (2015): 4289–95. http://dx.doi.org/10.1039/c5ob00131e.

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20

Aksenov, Alexander V., Nicolai A. Aksenov, Nikolai A. Arutiunov, Vladimir V. Malyuga, Sergey N. Ovcharov, and Michael Rubin. "Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines." RSC Advances 9, no. 67 (2019): 39458–65. http://dx.doi.org/10.1039/c9ra08630g.

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21

Schwieter, Kenneth E., and Jeffrey N. Johnston. "A one-pot amidation of primary nitroalkanes." Chemical Communications 52, no. 1 (2016): 152–55. http://dx.doi.org/10.1039/c5cc08415f.

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22

Marcé, Patricia, James Lynch, A. John Blacker, and Jonathan M. J. Williams. "Conversion of nitroalkanes into carboxylic acids via iodide catalysis in water." Chemical Communications 52, no. 5 (2016): 1013–16. http://dx.doi.org/10.1039/c5cc08681g.

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23

Palmieri, Alessandro, Serena Gabrielli, and Roberto Ballini. "Easy and direct conversion of tosylates and mesylates into nitroalkanes." Beilstein Journal of Organic Chemistry 9 (March 14, 2013): 533–36. http://dx.doi.org/10.3762/bjoc.9.58.

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24

Kumar, Akshay, Jasneet Kaur, Swapandeep Singh Chimni, and Amanpreet Kaur Jassal. "Organocatalytic enantioselective aza-Henry reaction of ketimines derived from isatins: access to optically active 3-amino-2-oxindoles." RSC Adv. 4, no. 47 (2014): 24816–19. http://dx.doi.org/10.1039/c4ra00902a.

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25

Uraguchi, Daisuke, Shinji Nakamura, Hitoshi Sasaki, Yuki Konakade та Takashi Ooi. "Enantioselective formal α-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction–Julia–Kocienski olefination sequence". Chem. Commun. 50, № 26 (2014): 3491–93. http://dx.doi.org/10.1039/c3cc49477b.

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26

Aksenov, Alexander V., Dmitrii S. Ovcharov, Nicolai A. Aksenov, Dmitrii A. Aksenov, Oleg N. Nadein, and Michael Rubin. "Dual role of polyphosphoric acid-activated nitroalkanes in oxidative peri-annulations: efficient synthesis of 1,3,6,8-tetraazapyrenes." RSC Advances 7, no. 48 (2017): 29927–32. http://dx.doi.org/10.1039/c7ra04751g.

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27

Aksenov, Nicolai A., Alexander V. Aksenov, Alexander Kornienko, et al. "A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities." RSC Advances 8, no. 64 (2018): 36980–86. http://dx.doi.org/10.1039/c8ra08155g.

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28

Aksenov, Alexander V., Nicolai A. Aksenov, Dmitrii S. Ovcharov, et al. "Rational design of an efficient one-pot synthesis of 6H-pyrrolo[2,3,4-gh]perimidines in polyphosphoric acid." RSC Advances 6, no. 85 (2016): 82425–31. http://dx.doi.org/10.1039/c6ra17269e.

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29

Yao, Wubing, Jiali Wang, Yinpeng Lou, et al. "Chemoselective hydroborative reduction of nitro motifs using a transition-metal-free catalyst." Organic Chemistry Frontiers 8, no. 16 (2021): 4554–59. http://dx.doi.org/10.1039/d1qo00705j.

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30

Susam, Dilşad, and Cihangir Tanyeli. "Enantioselective aza-Henry reaction of t-Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts." New Journal of Chemistry 41, no. 9 (2017): 3555–61. http://dx.doi.org/10.1039/c6nj04078k.

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31

Aksenov, Nicolai A., Alexander V. Aksenov, Nikita K. Kirilov, et al. "Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity." Organic & Biomolecular Chemistry 18, no. 34 (2020): 6651–64. http://dx.doi.org/10.1039/d0ob01007c.

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32

Mahato, Sachinta, Anindita Mukherjee, Sougata Santra, Grigory V. Zyryanov, and Adinath Majee. "Facile synthesis of substituted quinolines by iron(iii)-catalyzed cascade reaction between anilines, aldehydes and nitroalkanes." Organic & Biomolecular Chemistry 17, no. 34 (2019): 7907–17. http://dx.doi.org/10.1039/c9ob01294j.

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33

Aksenov, Alexander V., Vladislav Khamraev, Nicolai A. Aksenov, et al. "Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles." RSC Advances 9, no. 12 (2019): 6636–42. http://dx.doi.org/10.1039/c9ra00976k.

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34

Yang, Weisen, Li Wei, Tao Yan, and Mingzhong Cai. "Highly efficient heterogeneous aerobic oxidative C–C coupling from Csp3–H bonds by a magnetic nanoparticle-immobilized bipy–gold(iii) catalyst." Catalysis Science & Technology 7, no. 8 (2017): 1744–55. http://dx.doi.org/10.1039/c6cy02567f.

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35

Faverio, Chiara, Monica Fiorenza Boselli, Patricia Camarero Gonzalez, Alessandra Puglisi, and Maurizio Benaglia. "Nitroalkene reduction in deep eutectic solvents promoted by BH3NH3." Beilstein Journal of Organic Chemistry 17 (May 6, 2021): 1041–47. http://dx.doi.org/10.3762/bjoc.17.83.

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Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH3NH3, with bio-based eutectic mixtures as biorenewable solvents in the synthesis of nitroalkanes, valuable precursors of amines. A variety of nitrostyrenes and alkyl-substituted nitroalkenes, including α- and β-substituted nitroolefins, were chemoselectively reduced to the nitroalkanes, with an atom economy-oriented, simple and convenient experimental procedure. A reliable and easily reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated.

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36

Comeau, M., M. T. Béraldin, E. C. Vauthier, and S. Fliszár. "Charge distributions and chemical effects. XXXVIII. Correlations between nuclear magnetic resonance shifts and electronic charges of nitrogen atoms." Canadian Journal of Chemistry 63, no. 11 (1985): 3226–32. http://dx.doi.org/10.1139/v85-534.

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Correlations between nuclear magnetic resonance shifts and atomic charges of nitrogen in selected alkylamines, nitroalkanes, isonitriles, and azines consistently follow the general trends observed for carbon and oxygen nuclei. In azines, any increase in total electronic population on nitrogen, resulting from a gain in π charge prevailing over a concurrent loss of σ electrons, is accompanied by an upfield resonance shift—as found for aromatic and ethylenic carbon and carbonyl oxygen atoms. On the other hand, any gain in total charge dictated by that of σ populations translates into a downfield 15N shift, which is the trend exhibited by alkylamines, nitroalkanes, and isonitriles—a situation encountered earlier with sp3-hybridized carbon, carbonyl carbon, and dialkyl ether oxygen atoms.

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37

Peng, Chen-Jun, Jun-Ping Pei, Ying-Han Chen, Zhi-Yong Wu, Ming Liu, and Yan-Kai Liu. "Enantioselective organocatalytic sequential Michael-cyclization of functionalized nitroalkanes to 2-hydroxycinnamaldehydes: synthesis of benzofused dioxa[3.3.1] and oxa[4.3.1] methylene-bridged compounds." Organic Chemistry Frontiers 8, no. 15 (2021): 4217–23. http://dx.doi.org/10.1039/d1qo00501d.

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An organocatalytic enantioselective conjugate addition-initiated reaction sequence of 2-hydroxycinnamaldehydes with various functionalized nitroalkanes has been described to synthesize structurally diverse chromane-containing compounds.

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38

Kwiatkowski, Jacek, та Yixin Lu. "Asymmetric Michael addition of α-fluoro-α-nitroalkanes to nitroolefins: facile preparation of fluorinated amines and tetrahydropyrimidines". Chem. Commun. 50, № 66 (2014): 9313–16. http://dx.doi.org/10.1039/c4cc03513e.

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39

Gao, Wenchao, Hui Lv, Tonghuan Zhang та ін. "Nickel-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins: an efficient approach to chiral amines". Chemical Science 8, № 9 (2017): 6419–22. http://dx.doi.org/10.1039/c7sc02669b.

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The Ni-catalyzed asymmetric hydrogenation of challenging β-acylamino nitroolefins was achieved under mild conditions, affording β-acylamino nitroalkanes in excellent yields and with high enantioselectivities.

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40

Li, Xiu, He Zhao, Xiuwen Chen, Huanfeng Jiang та Min Zhang. "Copper-catalysed oxidative α-C(sp3)–H nitroalkylation of (hetero)arene-fused cyclic amines". Organic Chemistry Frontiers 7, № 2 (2020): 425–29. http://dx.doi.org/10.1039/c9qo01208g.

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41

Palmieri, Alessandro, Serena Gabrielli, Susanna Sampaolesi, and Roberto Ballini. "Nitroaldol (Henry) reaction of 2-oxoaldehydes with nitroalkanes as a strategic step for a useful, one-pot synthesis of 1,2-diketones." RSC Advances 5, no. 46 (2015): 36652–55. http://dx.doi.org/10.1039/c5ra03772g.

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42

Yu, Lin, Hang Huang, Xiang Chen, Liang Hu, Yongqi Yu, and Ze Tan. "Efficient syntheses of 3-hydroxyimino-1-isoindolinones and 3-methylene-1-isoindolinones via Cu-promoted C–H activation–nitroalkylation–intramolecular cyclization tandem processes." Chemical Communications 53, no. 33 (2017): 4597–600. http://dx.doi.org/10.1039/c7cc01097d.

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43

Aksenov, Dmitrii A., Nikolai A. Arutiunov, Vladimir V. Maliuga, Alexander V. Aksenov, and Michael Rubin. "Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes." Beilstein Journal of Organic Chemistry 16 (November 26, 2020): 2903–10. http://dx.doi.org/10.3762/bjoc.16.239.

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Imidazo[1,5-a]pyridines were efficiently prepared via the cyclization of 2-picolylamines with nitroalkanes electrophilically activated in the presence of phosphorous acid in polyphosphoric acid (PPA) medium.

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44

Grenning, Alexander J., and Jon A. Tunge. "Rapid Decarboxylative Allylation of Nitroalkanes." Organic Letters 12, no. 4 (2010): 740–42. http://dx.doi.org/10.1021/ol902828p.

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45

Blanco, Guillermo A., and Maria T. Baumgartner. "Sulfenylation of nitroalkanes and hydroxyaryls." Tetrahedron Letters 52, no. 52 (2011): 7061–63. http://dx.doi.org/10.1016/j.tetlet.2011.10.053.

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46

Kim, Raphael S., Linh V. Dinh-Nguyen, Kirk W. Shimkin, and Donald A. Watson. "Copper-Catalyzed Propargylation of Nitroalkanes." Organic Letters 22, no. 20 (2020): 8106–10. http://dx.doi.org/10.1021/acs.orglett.0c03061.

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47

Vogl, Erasmus M., and Stephen L. Buchwald. "Palladium-Catalyzed Monoarylation of Nitroalkanes." Journal of Organic Chemistry 67, no. 1 (2002): 106–11. http://dx.doi.org/10.1021/jo010953v.

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48

Yan, Qiaozhi, Man Liu, Duanyang Kong, Guofu Zi та Guohua Hou. "Highly efficient iridium-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins". Chem. Commun. 50, № 85 (2014): 12870–72. http://dx.doi.org/10.1039/c4cc05815a.

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A highly Ir-catalyzed enantioselective hydrogenation of β-acylamino nitroolefins is first reported, which provides straightforward access to chiral β-amino nitroalkanes in excellent enantioselectivities (up to >99.9% ee).

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49

Aksenov, Alexander V., Nicolai A. Aksenov, Nikita K. Kirilov, et al. "Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?" RSC Advances 11, no. 57 (2021): 35937–45. http://dx.doi.org/10.1039/d1ra06503c.

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Abstract:

The mechanistic rationale involving activation of nitroalkanes towards interaction with nucleophilic reagents in the presence of polyphosphoric acid (PPA) was re-evaluated. Could nitrile oxide moieties be formed during this process?

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50

Aksenov, Nicolai A., Alexander V. Aksenov, Oleg N. Nadein, Dmitrii A. Aksenov, Alexander N. Smirnov, and Michael Rubin. "One-pot synthesis of benzoxazoles via the metal-free ortho-C–H functionalization of phenols with nitroalkanes." RSC Advances 5, no. 88 (2015): 71620–26. http://dx.doi.org/10.1039/c5ra15128g.

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Abstract:

PPA-activated nitroalkanes are employed in the design of a one-pot cascade transformation involvingortho-C–H functionalization, by Beckman rearrangement, and condensation to produce benzoxazoles and benzobisoxazoles directly from phenols.

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