How to cite this paper
Łapczuk-Krygier, A., Kącka-Zych, A & Kula, K. (2019). Recent progress in the field of cycloaddition reactions involving conjugated nitroalkenes.Current Chemistry Letters, 8(1), 13-38.
Refrences
1. Kącka, A. B.; Jasiński, R. A. (2016) A Density Functional Theory Mechanistic Study of Thermal Decomposition Reactions of Nitroethyl Carboxylates: Undermine of “Pericyclic” Insight. Heteroat. Chem., 27 (5) 279–289.
2. Kącka-Zych A., Woliński P. (2018) Chemistry of 2-aryl-1-cyano-1-nitroethenes. Part II. Chemical transformations Tech. Trans., 2, 123-139
3. Schuhmann, I.; Yao, C. B. F. F.; Al-Zereini, W.; Anke, H.; Helmke, E.; Laatsch, H. Nitro (2009) Derivatives from the Arctic Ice Bacterium Salegentibacter Sp. Isolate T436. J. Antibiot. (Tokyo)., 62 (8) 453–460.
4. Barrett, A. G. M.; Graboski, G. G. (1986) Conjugated Nitroalkenes: Versatile Intermediates in Organic Synthesis. Chem. Rev., 86 (5) 751–762.
5. Perekalin, V. V. (1994) Nitroalkenes : Conjugated Nitro Compounds; Perekalin, Ed.; Wiley: New York.
6. Baichurin, R. I.; Aboskalova, N. I.; Trukhin, E. V.; Berestovitskaya, V. M. (2015) Aryl(Hetaryl)-Containing Gem-Cyanonitroethenes: Synthesis, Structure, and Reactions with 2,3-Dimethyl-1,3-Butadiene. Russ. J. Gen. Chem., 85 (8) 1845–1854.
7. Kącka, A. B.; Jasiński, R. A. (2016) A Density Functional Theory Mechanistic Study of Thermal Decomposition Reactions of Nitroethyl Carboxylates: Undermine of “Pericyclic” Insight. Heteroat. Chem., 27 (5) 279–289.
8. Jasiński, R.; Kącka, A. (2015) A Polar Nature of Benzoic Acids Extrusion from Nitroalkyl Benzoates: DFT Mechanistic Study. J. Mol. Model., 21 (3) 59.
9. Boguszewska-Czubara, A.; Łapczuk-Krygier, A.; Rykala, K.; Biernasiuk, A.; Wnorowski, A.; Popiolek, L.; Maziarka, A.; Hordyjewska, A.; Jasiński, R. (2016) Novel Synthesis Scheme and in Vitro Antimicrobial Evaluation of a Panel of (E)-2-Aryl-1-Cyano-1-Nitroethenes. J. Enzyme Inhib. Med. Chem., 31 (6) 900–907.
10. Jasiński, R. (2014) Molecular Mechanism of Thermal Decomposition of Fluoronitroazoxy Compounds: DFT Computational Study. J. Fluor. Chem., 160, 29–33.
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12. Korotaev, V. Y.; Barkov, A. Y.; Slepukhin, P. A.; Kodess, M. I.; Sosnovskikh, V. Y. (2011) Uncatalyzed Reactions of α-(Trihaloethylidene)Nitroalkanes with Push-Pull Enamines: A New Type of Ring-Ring Tautomerism in Cyclobutane Derivatives and the Dramatic Effect of the Trihalomethyl Group on the Reaction Pathway. Tetrahedron Lett., 52 (44) 5764–5768.
13. Albrecht, Ł.; Dickmeiss, G.; Acosta, F. C.; Rodr, C.; Davis, R. L.; Jørgensen, K. A. (2012)Asymmetric Organocatalytic Formal [2 + 2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis. J. Am. Chem.Soc. 134 (5) 2543−2546.
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15. Patora-Komisarska, K.; Benohoud, M.; Ishikawa, H.; Seebach, D.; Hayashi, Y. (2011) Organocatalyzed Michael Addition of Aldehydes to Nitro Alkenes - Generally Accepted Mechanism Revisited and Revised. Helv. Chim. Acta, 94 (5) 719–745.
16. Smith, D. L.; Chidipudi, S. R.; Goundry, W. R.; Lam, H. W. (2012) Rhodium-Catalyzed [2+2] Cycloaddition of Ynamides with Nitroalkenes. Org. Lett., 14 (18) 4934–4937.
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18. Dresler, E.; Jasiński, R. (2015) Synthesis of New 2-Aryl-3-Phenyl-4-Nitro-Tetrahydro-1,2-Oxazoles in 1,3-Dialkylimidazolium Ionic Liquid. Przem. Chem., 94 (12) 2244–2246.
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24. Jasiński, R.; Ziółkowska, M.; Demchuk, O. M.; Maziarka, A. (2014) Regio- and Stereoselectivity of Polar [2+3] Cycloaddition Reactions between (Z)-C-(3,4,5-Trimethoxyphenyl)-N-Methylnitrone and Selected (E)-2-Substituted Nitroethenes. Cent. Eur. J. Chem., 12 (5) 586–593.
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30. Sarrafi, Y.; Asghari, A.; Hamzehloueian, M.; Alimohammadi, K.; Sadatshahabi, M. (2013) A Facile Regioselective Synthesis of Novel Spiroacenaphthene Pyrroloisoquinolines Through 1,3-Dipolar Cycloaddition Reactions. J. Braz. Chem. Soc., 24 (12) 1957–1963.
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2. Kącka-Zych A., Woliński P. (2018) Chemistry of 2-aryl-1-cyano-1-nitroethenes. Part II. Chemical transformations Tech. Trans., 2, 123-139
3. Schuhmann, I.; Yao, C. B. F. F.; Al-Zereini, W.; Anke, H.; Helmke, E.; Laatsch, H. Nitro (2009) Derivatives from the Arctic Ice Bacterium Salegentibacter Sp. Isolate T436. J. Antibiot. (Tokyo)., 62 (8) 453–460.
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5. Perekalin, V. V. (1994) Nitroalkenes : Conjugated Nitro Compounds; Perekalin, Ed.; Wiley: New York.
6. Baichurin, R. I.; Aboskalova, N. I.; Trukhin, E. V.; Berestovitskaya, V. M. (2015) Aryl(Hetaryl)-Containing Gem-Cyanonitroethenes: Synthesis, Structure, and Reactions with 2,3-Dimethyl-1,3-Butadiene. Russ. J. Gen. Chem., 85 (8) 1845–1854.
7. Kącka, A. B.; Jasiński, R. A. (2016) A Density Functional Theory Mechanistic Study of Thermal Decomposition Reactions of Nitroethyl Carboxylates: Undermine of “Pericyclic” Insight. Heteroat. Chem., 27 (5) 279–289.
8. Jasiński, R.; Kącka, A. (2015) A Polar Nature of Benzoic Acids Extrusion from Nitroalkyl Benzoates: DFT Mechanistic Study. J. Mol. Model., 21 (3) 59.
9. Boguszewska-Czubara, A.; Łapczuk-Krygier, A.; Rykala, K.; Biernasiuk, A.; Wnorowski, A.; Popiolek, L.; Maziarka, A.; Hordyjewska, A.; Jasiński, R. (2016) Novel Synthesis Scheme and in Vitro Antimicrobial Evaluation of a Panel of (E)-2-Aryl-1-Cyano-1-Nitroethenes. J. Enzyme Inhib. Med. Chem., 31 (6) 900–907.
10. Jasiński, R. (2014) Molecular Mechanism of Thermal Decomposition of Fluoronitroazoxy Compounds: DFT Computational Study. J. Fluor. Chem., 160, 29–33.
11. Mohr, L. (2017) Intermolecular [2 + 2] Photocycloaddition of β -Nitrostyrenes to Olefins upon Irradiation with Visible Light. Synlett, 28 (20) 2946–2950.
12. Korotaev, V. Y.; Barkov, A. Y.; Slepukhin, P. A.; Kodess, M. I.; Sosnovskikh, V. Y. (2011) Uncatalyzed Reactions of α-(Trihaloethylidene)Nitroalkanes with Push-Pull Enamines: A New Type of Ring-Ring Tautomerism in Cyclobutane Derivatives and the Dramatic Effect of the Trihalomethyl Group on the Reaction Pathway. Tetrahedron Lett., 52 (44) 5764–5768.
13. Albrecht, Ł.; Dickmeiss, G.; Acosta, F. C.; Rodr, C.; Davis, R. L.; Jørgensen, K. A. (2012)Asymmetric Organocatalytic Formal [2 + 2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis. J. Am. Chem.Soc. 134 (5) 2543−2546.
14. Dobi, Z.; Holczbauer, T.; Soós, T. (2017) Schreiner’s Thiourea Promoted [2+2] Cycloaddition of Captodative Azetidinones and Nitroolefins. European J. Org. Chem., 17 (11) 1391–1395.
15. Patora-Komisarska, K.; Benohoud, M.; Ishikawa, H.; Seebach, D.; Hayashi, Y. (2011) Organocatalyzed Michael Addition of Aldehydes to Nitro Alkenes - Generally Accepted Mechanism Revisited and Revised. Helv. Chim. Acta, 94 (5) 719–745.
16. Smith, D. L.; Chidipudi, S. R.; Goundry, W. R.; Lam, H. W. (2012) Rhodium-Catalyzed [2+2] Cycloaddition of Ynamides with Nitroalkenes. Org. Lett., 14 (18) 4934–4937.
17. Jasiński, R. (2009) Regio- and Stereoselectivity of [2+3]Cycloaddition of Nitroethene to (Z)-N-Aryl-C-Phenylnitrones. Collect. Czechoslov. Chem. Commun., 74 (9) 1341–1349.
18. Dresler, E.; Jasiński, R. (2015) Synthesis of New 2-Aryl-3-Phenyl-4-Nitro-Tetrahydro-1,2-Oxazoles in 1,3-Dialkylimidazolium Ionic Liquid. Przem. Chem., 94 (12) 2244–2246.
19. Jasiński, R. (2009) The Question of the Regiodirection of the [2+3] Cycloaddition Reaction of Triphenylnitrone to Nitroethene. Chem. Heterocycl. Compd., 45 (6) 748–749.
20. Burdisso, M.; Gandolfi, R.; Grünanger, P. (1989) Control of Regiochemistry in Nitrone Cycloadditions. Regioselectivity of the Reactions of Trisubstituted Nitrones with Electron-Deficient and Conjugated Dipolarophiles. Tetrahedron, 45 (17) 5579–5594.
21. Jasiński, R. (2015) 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 Lett., 56 (3) 532–535.
22. Jasiński, R. (2007) Studia nad regioselektywnością [2+3] cykloaddycji C,C,N-trifenylonitronu z E-β-cyjanonitroetylenem. Czas. Tech., 104 (1) 5–9.
23. Bigotti, S.; Malpezzi, L.; Molteni, M.; Mele, A.; Panzeri, W.; Zanda, M. (2009) Functionalized Fluoroalkyl Heterocycles by 1,3-Dipolar Cycloadditions with γ-Fluoro-α-Nitroalkenes. Tetrahedron Lett., 50 (21) 2540–2542.
24. Jasiński, R.; Ziółkowska, M.; Demchuk, O. M.; Maziarka, A. (2014) Regio- and Stereoselectivity of Polar [2+3] Cycloaddition Reactions between (Z)-C-(3,4,5-Trimethoxyphenyl)-N-Methylnitrone and Selected (E)-2-Substituted Nitroethenes. Cent. Eur. J. Chem., 12 (5) 586–593.
25. Jasiński, R.; Mróz, K.; Kącka, A. (2015) 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. J. Heterocycl. Chem., 53 (5) 1424–1429.
26. Jasiński, R.; Mróz, K. (2015) Kinetic Aspects of [3+2] Cycloaddition Reactions between (E)-3,3,3-Trichloro-1-Nitroprop-1-Ene and Ketonitrones. React. Kinet. Mech. Catal., 116 (1) 35–41.
27. Jasiński, R. (2012) Competition between the One Step and Two-Step, Zwitterionic Mechanisms in the Cycloaddition of Gem-Dinitroethene with (Z)-C, N-Diphenylnitrone. Tetrahedron, 69 (2) 927-932.
28. Jasiński, R.; Jasińska, E.; Dresler, E. (2017) A DFT Computational Study of the Molecular Mechanism of [3+2] Cycloaddition Reactions between Nitroethene and Benzonitrile N-Oxides. J. Mol. Model., 23 (1) 13.
29. Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. (2000) Tandem in Situ Generation of Azomethine Ylides and Base Sensitive Nitroethylene Dipolarophiles. Tetrahedron, 56 (4) 639–644.
30. Sarrafi, Y.; Asghari, A.; Hamzehloueian, M.; Alimohammadi, K.; Sadatshahabi, M. (2013) A Facile Regioselective Synthesis of Novel Spiroacenaphthene Pyrroloisoquinolines Through 1,3-Dipolar Cycloaddition Reactions. J. Braz. Chem. Soc., 24 (12) 1957–1963.
31. Pechenkin, S. Y.; Starosotnikov, A. M.; Bastrakov, M. A.; Glukhov, I. V.; Sheveleva, S. A. (2012) 4-R-7-Nitrobenzofurazans in [3+2] Cycloaddition Reactions with N-Methylazomethine Ylide. Russ. Chem. Bull. Int. Ed., 61 (1) 74–77.
32. Syroeshkina, Y. S.; Kachala, V. V.; Ovchinnikov, I. V.; Kuznetsov, V. V.; Nelyubina, Y. V.; Lyssenko, K. A.; Makhova, N. N. (2009) Ionic-Liquids-Assisted Reaction of 6-Aryl-1,5-Diazabicyclo[3.1.0]Hexanes with β-Nitrostyrenes. Mendeleev Commun., 19 (5) 276–278.
33. Yang, D.; Fan, M.; Zhu, H.; Guo, Y.; Guo, J. (2013) Catalyst-Free and Stereoselective Synthesis of N,N-Bicyclic Pyrazolidinone Derivatives. Synth., 45 (10) 1325–1332.
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35. Jasiński, R.; Kula, K.; Kącka, A.; Mirosław, B. (2017) Unexpected Course of Reaction between (E)-2-Aryl-1-Cyano-1-Nitroethenes and Diazafluorene: Why Is There No 1,3-Dipolar Cycloaddition? Monatshefte fur Chemie, 148 (5) 909–915.
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