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Mendeleev Communications, 2008, Volume 18, Issue 5, Pages 255–257
DOI: https://doi.org/10.1016/j.mencom.2008.09.009
(Mi mendc3317)
 

This article is cited in 15 scientific papers (total in 15 papers)

Six-membered cyclic nitronates as Brönsted bases: protonation and rearrangement into butyrolactone oximes

V. O. Smirnov, Yu. A. Khomutova, S. L. Ioffe

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: The protonation of six-membered cyclic nitronates (SMCNs) was studied by low-temperature NMR spectroscopy, and an efficient preparative procedure for acid-induced rearrangement of SMCNs into oximes of substituted butyrolactones was developed.
Document Type: Article
Language: English


Citation: V. O. Smirnov, Yu. A. Khomutova, S. L. Ioffe, “Six-membered cyclic nitronates as Brönsted bases: protonation and rearrangement into butyrolactone oximes”, Mendeleev Commun., 18:5 (2008), 255–257
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  • https://www.mathnet.ru/eng/mendc/v18/i5/p255
  • This publication is cited in the following 15 articles:
    1. Stepan N. Ostarkov, Yana I. Lichtenstein, Yulia A. Antonova, Yulia V. Nelyubina, Vladislav K. Lesnikov, Andrey A. Tabolin, “Divergent Annulations of 5,6‐Dihydro‐4H‐1,2‐Oxazine N‐Oxides and Enol Diazoacetates for the Switchable Chemoselective Synthesis of Fused 1,2‐Oxazine Derivatives”, Eur J Org Chem, 27:45 (2024)  crossref
    2. Roman S. Malykhin, Alexey Yu. Sukhorukov, “Electrophilic Intermediates in the Nef and Meyer Reactions: A Computational Study”, J. Org. Chem., 2024  crossref
    3. Alexey Yu. Sukhorukov, “Interrupted Nef and Meyer Reactions: A Growing Point for Diversity-Oriented Synthesis Based on Nitro Compounds”, Molecules, 28:2 (2023), 686  crossref
    4. Max M. Majireck, John M. Bennett, Comprehensive Heterocyclic Chemistry IV, 2022, 283  crossref
    5. Roman S. Malykhin, Yaroslav D. Boyko, Yulia V. Nelyubina, Sema L. Ioffe, Alexey Yu. Sukhorukov, “Interrupted Nef Reaction of Cyclic Nitronates: Diastereoselective Access to Densely Substituted α-Chloronitroso Compounds”, J. Org. Chem., 87:24 (2022), 16617  crossref
    6. Tsung-Jung Jao, Pavan Sudheer Akula, Bor-Cherng Hong, Gene-Hsiang Lee, “Catalytic 1,2-Rearrangements: Organocatalyzed Michael/Semi-Pinacol-like Rearrangement Cascade of 1,3-Diones and Nitroolefins”, Org. Lett., 22:1 (2020), 62  crossref
    7. Roman S. Malykhin, Aleksandr O. Kokuev, Valentin S. Dorokhov, Yulia V. Nelyubina, Vladimir A. Tartakovsky, Andrey A. Tabolin, Sema L. Ioffe, Alexey Yu. Sukhorukov, “Nucleophilic Halogenation of Cyclic Nitronates: A General Access to 3-Halo-1,2-Oxazines”, J. Org. Chem., 84:21 (2019), 13794  crossref
    8. S. L. Ioffe, Yu. A. Khoroshutina, V. O. Smirnov, A. A. Mikhaylov, “A New Algorithm for the Reactivity Umpolung of Aliphatic Nitro Compounds”, Kinet Catal, 59:6 (2018), 691  crossref
    9. A. A. Tabolin, A. Yu. Sukhorukov, S. L. Ioffe, “α‐Electrophilic Reactivity of Nitronates”, The Chemical Record, 18:10 (2018), 1489  crossref
    10. A. A. Tabolin, E. O. Gorbacheva, R. A. Novikov, Yu. A. Khoroshutina, Yu. V. Nelyubina, S. L. Ioffe, “Synthesis and chemical transformations of six/six-membered bicyclic nitroso acetals”, Russ Chem Bull, 65:9 (2016), 2243  crossref
    11. Qing-Fa Zhou, Kui Zhang, Lingchao Cai, Ohyun Kwon, “Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes”, Org. Lett., 18:12 (2016), 2954  crossref
    12. Pritam Biswas, Jaydip Ghosh, Sourav Maiti, Subhabrata Banerjee, Chandrakanta Bandyopadhyay, “Substituent-controlled domino-Henry-hetero Diels–Alder reaction: synthesis of polycyclic nitronates”, Tetrahedron Letters, 54:26 (2013), 3466  crossref
    13. Andrey A. Mikhaylov, Alexander D. Dilman, Marina I. Struchkova, Yulia A. Khomutova, Alexander A. Korlyukov, Sema L. Ioffe, Vladimir A. Tartakovsky, “3-Halomethylated cyclic nitronates: synthesis and nucleophilic substitution”, Tetrahedron, 67:25 (2011), 4584  crossref
    14. Andrey A. Mikhaylov, Alexander D. Dilman, Roman A. Kunetsky, Yulia A. Khomutova, Marina I. Struchkova, Alexander A. Korlyukov, Sema L. Ioffe, Vladimir A. Tartakovsky, “Synthesis and reactions of 3-halomethyl-substituted oxazine N-oxides”, Tetrahedron Letters, 51:7 (2010), 1038  crossref
    15. Vladimir O. Smirnov, Yulia A. Khomutova, Sema L. Ioffe, “ChemInform Abstract: Six‐Membered Cyclic Nitronates as Broensted Bases: Protonation and Rearrangement into Butyrolactone Oximes.”, ChemInform, 40:13 (2009)  crossref
    Citing articles in Google Scholar: Russian citations, English citations
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