This article is cited in 14 scientific papers (total in 14 papers)
Intramolecular Inversion of Configuration at Tetrahedral Carbon Centres in Dipolar Spiro-σ-Complexes of Amino-, Diamino- and Aminothiotropones: a Dynamic NMR Spectral Study
Abstract:
Inversion of configuration at the tetrahedral carbon centres of dipolar spiro-σ-complexes formed by coupling 2-(N-benzylamino)tropone, 2-(N-benzylamino)thiotropone or N,N’-dibenzyl-2-aminotroponimine with electrophilic aromatic and heterocyclic compounds has been found to occur intramolecularly with energy barriers accessible to measurement by means of dynamic 1H NMR spectral techniques.
Document Type:
Article
Language: English
Citation:
L. P. Olekhnovich, Z. N. Budarina, A. V. Lesin, S. V. Kurbatov, G. S. Borodkin, V. I. Minkin, “Intramolecular Inversion of Configuration at Tetrahedral Carbon Centres in Dipolar Spiro-σ-Complexes of Amino-, Diamino- and Aminothiotropones: a Dynamic NMR Spectral Study”, Mendeleev Commun., 4:5 (1994), 162–164
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This publication is cited in the following 14 articles:
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Kirill Nikitin, Elizabeth V. Jennings, Sulaiman Al Sulaimi, Yannick Ortin, Declan G. Gilheany, “Dynamic Cross‐Exchange in Halophosphonium Species: Direct Observation of Stereochemical Inversion in the Course of an SN2 Process”, Angew Chem Int Ed, 57:6 (2018), 1480
Anna V. Tkachuk, Sergey V. Kurbatov, Pavel G. Morozov, Gennadiy S. Borodkin, “The first dipolar spirocycle based on 10-(benzylamino)colchicine”, Chem Heterocycl Comp, 51:10 (2015), 948
Angélique Lindamulage De Silva, Vesna Risso, Marion Jean, Michel Giorgi, Valérie Monnier, Jean‐Valère Naubron, Nicolas Vanthuyne, Daniel Farran, Christian Roussel, “A Forgotten Chiral Spiro Compound Revisited: 3,3'‐Dimethyl‐3H,3'H‐2,2'‐spirobi[[1,3]benzothiazole]”, Chirality, 27:10 (2015), 716
V. I. Minkin, A. V. Tkachuk, M. E. Kletskii, D. V. Steglenko, V. A. Voronina, S. V. Kurbatov, “Intramolecular π-complexes based on nitroaryl derivatives of furotroponimine: structure and stereodynamics”, Russ Chem Bull, 62:2 (2013), 464
P. G. Morozov, S. V. Kurbatov, “Determination of the R ⇄ S enantiomerization barrier in 5,6-dihydrobenzoimidazo[1,2-c]quinazolines”, Chem Heterocycl Comp, 48:5 (2012), 758
Dmitry V. Steglenko, Mikhail E. Kletsky, Sergey V. Kurbatov, Artem V. Tatarov, Vladimir I. Minkin, Régis Goumont, François Terrier, “A theoretical and experimental study of the polar Diels–Alder cycloaddition of cyclopentadiene with nitrobenzodifuroxan”, J of Physical Organic Chem, 22:4 (2009), 298
Luciano Forlani, Aline Laure Tocke, Erminia Del Vecchio, Sami Lakhdar, Régis Goumont, François Terrier, “Assessing the Nitrogen and Carbon Nucleophilicities of 2-Aminothiazoles through Coupling with Superelectrophilic 4,6-Dinitrobenzofuroxan”, J. Org. Chem., 71:15 (2006), 5527
Serguey Kurbatov, Régis Goumont, Sami Lakhdar, Jérome Marrot, François Terrier, “4-Nitrobenzodifuroxan: a highly reactive nitroolefin in Diels–Alder reactions”, Tetrahedron, 61:34 (2005), 8167
Vladimir I. Minkin, “Photo-, Thermo-, Solvato-, and Electrochromic Spiroheterocyclic Compounds”, Chem. Rev., 104:5 (2004), 2751
P. G. Morozov, S. V. Kurbatov, F. M. Dolgushin, M. Yu. Antipin, L. P. Olekhnovich, “Synthesis and structures of spiro-σ-complexes based on 2-(2-benzylaminophenyl)-5,6-dimethylbenzimidazole”, Russ Chem Bull, 53:9 (2004), 2075
Taoufik Boubaker, Alain Pierre Chatrousse, François Terrier, Bahoueddine Tangour, Julian M. Dust, Erwin Buncel, “Water and hydroxide ion pathways in the σ-complexation of superelectrophilic 2-aryl-4,6-dinitrobenzotriazole 1-oxides in aqueous solution. A kinetic and thermodynamic study”, J. Chem. Soc., Perkin Trans. 2, 2002, no. 9, 1627
Régis Goumont, Muriel Sebban, Patricia Sépulcri, Jérome Marrot, François Terrier, “The Diels–Alder reactivity of nitrobenzofuroxans: mono- and di-adducts of isoprene and 2,3-dimethylbutadiene. New convenient precursors to naphtho- and phenanthreno-furoxanic and -furazanic structures”, Tetrahedron, 58:16 (2002), 3249
S. V. Kurbatov, Z. N. Budarina, G. S. Vaslyaeva, N. I. Borisenko, A. P. Knyazev, V. I. Minkin, Yu. A. Zhdanov, L. P. Olekhnovich, “Dipolar spirocyclic σ-complexes based on of 4,6-dinitrobenzofuroxan”, Russ Chem Bull, 46:8 (1997), 1445
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