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Collect. Czech. Chem. Commun. 2009, 74, 1341-1349
https://doi.org/10.1135/cccc2009037
Published online 2009-09-11 22:41:43

Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones

Radomir Jasiński

Institute of Organic Chemistry and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Cracow, Poland

Crossref Cited-by Linking

  • Jasiński Radomir: Recent progress in the synthesis of nitroisoxazoles and their hydrogenated analogs via [3+2] cycloaddition reactions (microreview). Chem Heterocycl Comp 2023, 59, 730. <https://doi.org/10.1007/s10593-024-03262-x>
  • Kącka-Zych Agnieszka, Jasiński Radomir: A DFT study on the molecular mechanism of the conjugated nitroalkenes polymerization process initiated by selected unsaturated nucleophiles. Theor Chem Acc 2020, 139. <https://doi.org/10.1007/s00214-020-02627-7>
  • Li Youfeng, Tang Jin, Li Xiaofang: Synthesis of 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones via 1,3-dipolar cycloaddition reaction involving (Z)-C-aryl-N-phenylnitrones. Chem Heterocycl Comp 2020, 56, 1062. <https://doi.org/10.1007/s10593-020-02774-6>
  • Jasiński Radomir: Selenyl analog of the (Z)-C,N-diphenylnitrone as the TAC in [3 + 2] cycloaddition with nitroethene: A DFT computational study. Phosphorus, Sulfur, and Silicon and the Related Elements 2020, 195, 871. <https://doi.org/10.1080/10426507.2020.1760865>
  • Jasiński Radomir, Dresler Ewa: On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions: A Critical Review. Organics 2020, 1, 49. <https://doi.org/10.3390/org1010005>
  • Jasiński Radomir: Understanding of the molecular mechanism of the phenylsulfenic acid elimination from nitroalkyl systems. Journal of Molecular Graphics and Modelling 2019, 89, 109. <https://doi.org/10.1016/j.jmgm.2019.03.007>
  • Eberlin Ludovic, Macé Aurélie, Batsanov Andrei S., Carboni Bertrand, Whiting Andrew: A Dienyl Boronate‐Aryl Nitroso Ene Reaction Entry to C‐Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines. ChemistrySelect 2018, 3, 4557. <https://doi.org/10.1002/slct.201800945>
  • Dresler Ewa, Kącka-Zych Agnieszka, Kwiatkowska Magdalena, Jasiński Radomir: Regioselectivity, stereoselectivity, and molecular mechanism of [3 + 2] cycloaddition reactions between 2-methyl-1-nitroprop-1-ene and (Z)-C-aryl-N-phenylnitrones: a DFT computational study. J Mol Model 2018, 24. <https://doi.org/10.1007/s00894-018-3861-y>
  • Jasiński Radomir: Competition between one-step and two-step mechanism in polar [3 + 2] cycloadditions of (Z)-C-(3,4,5-trimethoxyphenyl)-N-methyl-nitrone with (Z)-2-EWG-1-bromo-1-nitroethenes. Computational and Theoretical Chemistry 2018, 1125, 77. <https://doi.org/10.1016/j.comptc.2018.01.009>
  • Jasiński Radomir: β-Trifluoromethylated nitroethenes in Diels-Alder reaction with cyclopentadiene: A DFT computational study. Journal of Fluorine Chemistry 2018, 206, 1. <https://doi.org/10.1016/j.jfluchem.2017.12.008>
  • Jasiński Radomir, Żmigrodzka Magdalena, Dresler Ewa, Kula Karolina: A Full Regioselective and Stereoselective Synthesis of 4‐Nitroisoxazolidines via Stepwise [3 + 2] Cycloaddition Reactions between (Z)‐C‐(9‐Anthryl)‐N‐arylnitrones and (E)‐3,3,3‐Trichloro‐1‐nitroprop‐1‐ene: Comprehensive Experimental and Theoretical Study. Journal of Heterocyclic Chem 2017, 54, 3314. <https://doi.org/10.1002/jhet.2951>
  • Jasiński Radomir, Kula Karolina, Kącka Agnieszka, Mirosław Barbara: Unexpected course of reaction between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?. Monatsh Chem 2017, 148, 909. <https://doi.org/10.1007/s00706-016-1893-5>
  • Jasiński Radomir, Jasińska Ewa, Dresler Ewa: A DFT computational study of the molecular mechanism of [3 + 2] cycloaddition reactions between nitroethene and benzonitrile N-oxides. J Mol Model 2017, 23. <https://doi.org/10.1007/s00894-016-3185-8>
  • Kącka Agnieszka, Jasiński Radomir: A dramatic change of kinetic conditions and molecular mechanism of decomposition processes of nitroalkyl carboxylates catalyzed by ethylammonium cations. Computational and Theoretical Chemistry 2017, 1104, 37. <https://doi.org/10.1016/j.comptc.2017.02.008>
  • Jasiński Radomir: One-step versus two-step mechanism of Diels-Alder reaction of 1-chloro-1-nitroethene with cyclopentadiene and furan. Journal of Molecular Graphics and Modelling 2017, 75, 55. <https://doi.org/10.1016/j.jmgm.2017.04.008>
  • Jasiński Radomir, Mróz Kamila, Kącka Agnieszka: Experimental and Theoretical DFT Study on Synthesis of Sterically Crowded 2,3,3,(4)5‐Tetrasubstituted‐4‐nitroisoxazolidines via 1,3‐Dipolar Cycloaddition Reactions Between Ketonitrones and Conjugated Nitroalkenes. Journal of Heterocyclic Chem 2016, 53, 1424. <https://doi.org/10.1002/jhet.2442>
  • Jasiński Radomir: Synthesis and Properties of Azoles and Their Derivatives. Part 70. Nitroallylic Systems in [2 + 3] Cycloaddition Reactions with Nitrones: A DFT Computational Study. Journal of Heterocyclic Chem 2015, 52, 185. <https://doi.org/10.1002/jhet.2020>
  • Jasiński Radomir: Nitroacetylene as dipolarophile in [2 + 3] cycloaddition reactions with allenyl-type three-atom components: DFT computational study. Monatsh Chem 2015, 146, 591. <https://doi.org/10.1007/s00706-014-1389-0>
  • Jasiński Radomir: On the question of zwitterionic intermediates in 1,3-dipolar cycloadditions between hexafluoroacetone and sterically crowded diazocompounds. Journal of Fluorine Chemistry 2015, 176, 35. <https://doi.org/10.1016/j.jfluchem.2015.04.020>
  • Jasiński Radomir: A stepwise, zwitterionic mechanism for the 1,3-dipolar cycloaddition between (Z)-C-4-methoxyphenyl-N-phenylnitrone and gem-chloronitroethene catalysed by 1-butyl-3-methylimidazolium ionic liquid cations. Tetrahedron Letters 2015, 56, 532. <https://doi.org/10.1016/j.tetlet.2014.12.007>
  • Jasiński Radomir: A new mechanistic insight on β-lactam systems formation from 5-nitroisoxazolidines. RSC Adv. 2015, 5, 50070. <https://doi.org/10.1039/C5RA07663C>
  • Jasiński Radomir: Competition between the one-step and two-step, zwitterionic mechanisms in the [2+3] cycloaddition of gem-dinitroethene with (Z)-C,N-diphenylnitrone: a DFT computational study. Tetrahedron 2013, 69, 927. <https://doi.org/10.1016/j.tet.2012.10.095>
  • Jasiński Radomir, Koifman Oskar I., Barański Andrzej: A DFT study on the regioselectivity and molecular mechanism of nitroethene [2 + 3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone. MENDELEEV COMMUN 2011, 21, 262. <https://doi.org/10.1016/j.mencom.2011.09.010>
  • Jasinski Radomir: ChemInform Abstract: Synthesis and Properties of Azoles and Their Derivatives. Part 67. Regio‐ and Stereoselectivity of [2 + 3]Cycloaddition of Nitroethene to (Z)‐N‐Aryl‐C‐phenylnitrones. ChemInform 2010, 41. <https://doi.org/10.1002/chin.201008134>
  • Mikulska M., Jasiński R., Barański A.: Synthesis and properties of azoles and their derivatives. 68.* [2+3] cycloaddition of 2-nitro-1-propene to (Z)-C,N-diphenylnitrone relative to AM1 and AM1/COSMO quantum-chemical calculations. Chem Heterocycl Comp 2010, 46, 232. <https://doi.org/10.1007/s10593-010-0496-z>