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Usp. Khim., 2006, Volume 75, Issue 11, Pages 1045–1073 (Mi rcr371)  

This article is cited in 40 scientific papers (total in 40 papers)

Theoretical studies on [3+2]-cycloaddition reactions

M. L. Kuznetsov

Department of Chemistry, Moscow State Pedagogical University

Abstract: The results of theoretical studies on [3+2]-cycloaddition reactions carried out during the last decade are summarised. The reaction mechanisms are discussed. The catalyst, solvent, and substituent effects on the reactivities of compounds and on the mechanisms, regioselectivity and stereoselectivity of reactions are considered. The results of theoretical studies are compared with corresponding experimental data.

Full text: http://www.uspkhim.ru/.../paper_rus.phtml?journal_id=rc&paper_id=1195

English version:
Russian Chemical Reviews, 2006, 75:11, 935–960

Bibliographic databases:

Document Type: Article
Received: 10.03.2005

Citation: M. L. Kuznetsov, “Theoretical studies on [3+2]-cycloaddition reactions”, Usp. Khim., 75:11 (2006), 1045–1073; Russian Chem. Reviews, 75:11 (2006), 935–960

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    Citing articles on Google Scholar: Russian citations, English citations
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    This publication is cited in the following articles:
    1. M. L. Kuznetsov, “Theoretical Studies on [3 + 2]-Cycloaddition Reactions”, ChemInform, 38:17 (2007)  crossref
    2. Kuznetsov M.L., Nazarov A.A., Kozlova L.V., Kukushkin V.Yu., “Theoretical Study of Chemo-, Regio-, and Stereoselectivity in 1,3-Dipolar Cycloadditions of Nitrones and Nitrile Oxides to Free and Pt-Bound Bifunctional Dipolarophiles”, J. Org. Chem., 72:12 (2007), 4475–4485  crossref  isi  elib  scopus
    3. Maxim L. Kuznetsov, Vadim Yu. Kukushkin, Armando J. L. Pombeiro, “Reactivity of Pt- and Pd-bound nitriles towards nitrile oxides and nitrones: substitution vs. cycloaddition”, Dalton Trans, 2008, no. 10, 1312  crossref  isi
    4. Baranski A., Lyubimtsev A., Jasinski R., Kwiatkowska M., “Synthesis and Properties of Azoles and their Derivatives. Part Lxii. Secondary Deuterium Kinetic Isotope Effects in [2+3] Cycloaddition of (E)-2-Phenylnitroethene to (Z)-C,N-Diphenylnitrone”, Pol. J. Chem., 82:5 (2008), 1037–1042  isi
    5. Jasinski R., Baranski A., “Synthesis and Properties of Azoles and their Derivatives. Part Lxiv. [2+3] Cycloaddition of Trans-1-Nitropropene-1 to C,C,N-Triphenylnitrone in the Light of Am1/Cosmo Calculations”, Pol. J. Chem., 82:5 (2008), 1043–1049  isi
    6. Sabirov D.Sh., Bulgakov R.G., Khursan S.L., Dzhemilev U.M., “A New Approach to the Estimation of the Fullerene Reactivity in 1,3-Dipolar Addition Based on Polarizability Indices”, Dokl. Phys. Chem., 425 (2009), 54–56  crossref  zmath  isi  elib  scopus
    7. Kuznetsov M.L. Bokach N.A. Kukushkin V.Yu. Dement'ev A.I., “Theoretical Study of Ammonia Nucleophilic Addition to Nitriles in Platinum Complexes”, Russ. J. Gen. Chem., 79:2 (2009), 232–241  crossref  isi  elib  scopus
    8. Menezes F.M.C., Kuznetsov M.L., Pombeiro A.J.L., “Isocyanide Complexes with Platinum and Palladium and their Reactivity Toward Cycloadditions with Nitrones to Form Aminooxycarbenes: a Theoretical Study”, Organometallics, 28:22 (2009), 6593–6602  crossref  isi  elib  scopus
    9. Ozen C., Konuklar F. Aylin S., Tuzun N.S., “Mechanistic Study on [3+2] Cycloaddition and Cyclopropanation Reactions of 1,3-Dioxepine Derivatives in the Presence of Copper(I) Catalyst”, Organometallics, 28:17 (2009), 4964–4973  crossref  isi  elib  scopus
    10. Lydia Rhyman, Hassan H. Abdallah, Sabina Jhaumeer-Laulloo, Luis R. Domingo, John A. Joule, Ponnadurai Ramasami, “The 1,3-dipolar cycloaddition of 1H-pyridinium-3-olate and 1-methylpyridinium-3-olate with methyl acrylate: a density functional theory study”, Tetrahedron, 66:47 (2010), 9187  crossref  isi  scopus
    11. Kuznetsov M.L. Bokach N.A. Kharlampidi D.D. Medvedev Yu.N. Kukushkin V.Yu. Dementiev A.I., “Theoretical Study of Nucleophilic Addition of Amines to Organic Nitriles”, Russ. J. Gen. Chem., 80:3 (2010), 458–467  crossref  isi  elib  scopus
    12. Kuznetsov M.L., Kukushkin V.Yu., Pombeiro A.J.L., “Comparative Theoretical Study of 1,3-Dipolar Cycloadditions of Allyl-Anion Type Dipoles to Free and Pt-Bound Nitriles”, J. Org. Chem., 75:5 (2010), 1474–1490  crossref  isi  elib  scopus
    13. Bokach N.A., “Cycloaddition of Nitrones To Metal-Activated Nitriles and Isocyanides”, Russ. Chem. Rev., 79:2 (2010), 89–100  mathnet  crossref  isi  elib  scopus
    14. Nadezhda A. Bokach, Maxim L. Kuznetsov, Vadim Yu. Kukushkin, “1,3-Dipolar cycloaddition of nitrone-type dipoles to uncomplexed and metal-bound substrates bearing the CN triple bond”, Coordination Chemistry Reviews, 2011  crossref  isi  scopus
    15. Starosotnikov A.M., Khakimo D.V., Bastrakov M.A., Pechenkin S.Yu., Shevelev S.A., Pivina T.S., “Special Features of 1,3-Dipolar Cycloaddition of N-Methylazomethinylid to Nitrobenzazoles”, Chem. Heterocycl. Compds., 47:2 (2011), 215–221  crossref  isi  scopus
    16. Talipov M.R. Khursan S.L. Safiullin R.L., “The Reaction of Nitroso Oxides with Olefins: Concerted Or Nonconcerted Addition?”, Russ. J. Phys. Chem. A, 85:3 (2011), 364–376  crossref  isi  elib  scopus
    17. Abraham I., Joshi R., Pardasani P., Pardasani R.T., “Recent Advances in 1,4-Benzoquinone Chemistry”, J. Braz. Chem. Soc., 22:3 (2011), 385–421  crossref  isi  elib  scopus
    18. Belen'kii L.I. Gramenitskaya V.N. Evdokimenkova Yu.B., “The Literature of Heterocyclic Chemistry, Part X, 2005-2007”, Advances in Heterocyclic Chemistry, Vol 102, Adv. Heterocycl. Chem., 102, ed. Katritzky A., 2011, 1–137  crossref  isi  scopus
    19. Andreii S. Kritchenkov, Nadezhda A. Bokach, Galina L. Starova, Vadim Yu. Kukushkin, “A Palladium(II) Center Activates Nitrile Ligands toward 1,3-Dipolar Cycloaddition of Nitrones Substantially More than the Corresponding Platinum(II) Center”, Inorg. Chem, 2012, 1210111125  crossref  isi  scopus
    20. Novikov A.S. Dement'ev A.I. Medvedev Yu.N., “Theoretical Study of Rh(I) and Rh(III) Bis(Isonitrile) Complexes as Promising Reagents for Synthesis of N-Heterocyclic Carbenes”, Russ. J. Inorg. Chem., 57:12 (2012), 1576–1583  crossref  isi  elib  scopus
    21. Mindich A.L., Bokach N.A., Kuznetsov M.L., Haukka M., Zhdanov A.P., Zhizhin K.Yu., Miltsov S.A., Kuznetsov N.T., Kukushkin V.Yu., “Coupling of Azomethine Ylides with Nitrilium Derivatives of Closo-Decaborate Clusters: a Synthetic and Theoretical Study”, ChemPlusChem, 77:12 (2012), 1075–1086  crossref  isi  elib  scopus
    22. Alexander S. Novikov, Maxim L. Kuznetsov, Armando J. L. Pombeiro, “Theory of the Formation and Decomposition of N-Heterocyclic Aminooxycarbenes through Metal-Assisted [2+3]-Dipolar Cycloaddition/Retro-Cycloaddition”, Chem. Eur. J, 2013, n/a  crossref  isi  scopus
    23. Shevelev S.A., Starosotnikov A.M., “Pericyclic [4+2] and [3+2] Cycloaddition Reactions of Nitroarenes in Heterocyclic Synthesis”, Chem. Heterocycl. Compds., 49:1 (2013), 92–115  crossref  isi  scopus
    24. Novikov A.S., Dement'ev A.I., Medvedev Yu.N., “Theoretical Study of the Reactivity of Rh(I) and Rh(III) Bis(Isonitrile) Complexes in Cycloaddition Reactions with Nitrones”, Russ. J. Inorg. Chem., 58:3 (2013), 320–330  crossref  isi  elib  scopus
    25. Bokach N.A., Kukushkin V.Yu., “Coordination Chemistry of Dialkylcyanamides: Binding Properties, Synthesis of Metal Complexes, and Ligand Reactivity”, Coord. Chem. Rev., 257:15-16 (2013), 2293–2316  crossref  isi  elib  scopus
    26. Wang J.-m., Li Zh.-m., Wang Q.-r., Tao F.-g., “A Dft Study on the Mechanisms for the Cycloaddition Reactions Between 1-Aza-2-Azoniaallene Cations and Acetylenes”, J. Mol. Model., 19:1 (2013), 83–95  crossref  adsnasa  isi  elib  scopus
    27. I. N. Klochkova, M. P. Shchekina, A. A. Anis’kov, “Synthesis of Spiropyrrolidines and Spiropyrrolizidines from Azomethine Ylides”, Chem Heterocycl Comp, 2014  crossref  isi  elib  scopus
    28. D.S.h. Sabirov, “Polarizability as a landmark property for fullerene chemistry and materials science”, RSC Adv, 4:85 (2014), 44996  crossref  isi  elib  scopus
    29. Tian Z., Xiao Yu., Yuan X., Chen Z., Zhang J., Ma J., “Control of Chemoselectivity By Coordinated Water and Relative Size of Ligands To Metal Cations of Lewis Acid Catalysts For Cycloaddition of An Oxirane Derivative To An Aldehyde: Theoretical and Experimental Study”, Organometallics, 33:7 (2014), 1715–1725  crossref  isi  elib  scopus
    30. Demakova M.Ya., Bolotin D.S., Bokach N.A., Starova G.L., Kukushkin V.Yu., “Metal-Mediated Cyanamide-Hydroxyguanidine Coupling”, Inorg. Chim. Acta, 425 (2015), 114–117  crossref  isi  scopus
    31. Adel Reisi-Vanani, Somayeh Rahimi, S.N.asiri Kokhdan, Hossein Ebrahimpour-Komleh, “Computational study of the gas phase reaction of hydrogen azide and corannulene: A DFT study”, Computational and Theoretical Chemistry, 2015  crossref  isi  scopus
    32. Siadati S.A., “Effect of Steric Congestion on the Stepwise Character and Synchronicity of a 1,3-Dipolar Reaction of a Nitrile Ylide and An Olefin”, J. Chem. Res, 2015, no. 11, 640–644  crossref  isi  scopus
    33. Siadati S.A., “The Effect of Position Replacement of Functional Groups on the Stepwise character of 1,3-Dipolar Reaction of a Nitrile Oxide and an Alkene”, Helv. Chim. Acta, 99:4 (2016), 273–280  crossref  isi  scopus
    34. Siadati S.A., Amini-Fazl M.S., Babanezhad E., “The possibility of sensing and inactivating the hazardous air pollutant species via adsorption and their [2 + 3] cycloaddition reactions with C 20 fullerene”, Sens. Actuator B-Chem., 237 (2016), 591–596  crossref  isi  scopus
    35. Siadati S.A., “Beyond the alternatives that switch the mechanism of the 1,3-dipolar cycloadditions from concerted to stepwise or vice versa: a literature review”, Prog. React. Kinet. Mech., 41:4 (2016), 331–344  crossref  isi  scopus
    36. Otero-Fraga J., Montesinos-Magraner M., Mendoza A., “Perspectives on Intermolecular Azomethine Ylide [3+2] Cycloadditions with Non-Electrophilic Olefins”, Synthesis, 49:4 (2017), 802–809  crossref  isi  scopus
    37. Melekhova A.A. Smirnov A.S. Novikov A.S. Panikorovskii T.L. Bokach N.A. Kukushkin V.Yu., “Copper(i)-Catalyzed 1,3-Dipolar Cycloaddition of Ketonitrones to Dialkylcyanamides: a Step Toward Sustainable Generation of 2,3 Dihydro-1,2,4-Oxadiazoles”, ACS Omega, 2:4 (2017), 1380–1391  crossref  isi  scopus
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