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Mendeleev Communications, 2017, Volume 27, Issue 3, Pages 293–295
DOI: https://doi.org/10.1016/j.mencom.2017.05.026
(Mi mendc1973)
 

This article is cited in 9 scientific papers (total in 9 papers)

Communications

Stereochemistry and mechanism of oxidative 1,4-addition of trifluoroacetamide to 2,3-dimethylbuta-1,3-diene

V. V. Astakhova, M. Yu. Moskalik, I. V. Sterkhova, B. A. Shainyan

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation
Full-text PDF (344 kB) Citations (9)
Abstract: Oxidative addition of trifluoroacetamide to 2,3-dimethylbuta-1,3-diene leads to N,N’-[(2E)-2,3-dimethylbut-2-ene-1,4-diyl]bis(trifluoroacetamide) and [(2RS,3SR)-N-(2,3-dihydroxy-4-iodo-2,3-dimethylbutyl)trifluoroacetamide. A tentative mechanism is proposed.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (1.1 Mb)


Citation: V. V. Astakhova, M. Yu. Moskalik, I. V. Sterkhova, B. A. Shainyan, “Stereochemistry and mechanism of oxidative 1,4-addition of trifluoroacetamide to 2,3-dimethylbuta-1,3-diene”, Mendeleev Commun., 27:3 (2017), 293–295
Linking options:
  • https://www.mathnet.ru/eng/mendc1973
  • https://www.mathnet.ru/eng/mendc/v27/i3/p293
  • This publication is cited in the following 9 articles:
    1. Vera V. Astakhova, Mikhail Yu. Moskalik, Bagrat A. Shainyan, “Reactions of carboxamides with vinylsilanes under oxidative conditions”, Journal of Organometallic Chemistry, 960 (2022), 122230  crossref
    2. Bagrat A. Shainyan, “N-Heterocycles via oxidative intramolecular cyclization”, Russian Chem. Reviews, 91:9 (2022), RCR5052  mathnet  mathnet  crossref  isi  scopus
    3. I. V. Sterkhova, V. V. Astakhova, I. M. Lazarev, “N,N-(2,3-Dimethylbut-2-ene-1,4-dienyl)dibenzenesulfonamide and N,N′-[(2E)-2,3-Dimethylbut-2-ene-1,4-dienyl]bis(trifluoroacetamide): Special Features of Hydrogen Bonding in the Crystal and Solutions”, Russ J Gen Chem, 91:6 (2021), 1009  crossref
    4. I. V. Sterkhova, I. M. Lazarev, B. A. Shainyan, “N-(2,3-Dihydroxy-4-iodo-2,3-dimethylbutyl)trifluoroacetamide: Hydrogen Bonds in Crystal and Solution”, Russ J Gen Chem, 89:8 (2019), 1564  crossref
    5. L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, E. V. Tretyakov, V. E. Platonov, P. V. Nikul'shin, A. S. Vinogradov, Ya. V. Zonov, V. M. Karpov, T. V. Mezhenkova, A. V. Vasilyev, A. B. Koldobskii, O. S. Shilova, S. M. Morozova, Ya. V. Burgart, E. V. Shchegolkov, V. I. Saloutin, V. B. Sokolov, A. Yu. Aksinenko, V. G. Nenajdenko, M. Yu. Moskalik, V. V. Astakhova, B. A. Shainyan, A. A. Tabolin, S. L. Ioffe, V. M. Muzalevskiy, E. S. Balenkova, A. V. Shastin, A. A. Tyutyunov, V. E. Boiko, S. M. Igumnov, A. D. Dilman, N. Yu. Adonin, V. V. Bardin, S. M. Masoud, D. V. Vorobyeva, S. N. Osipov, E. V. Nosova, G. N. Lipunova, V. N. Charushin, D. O. Prima, A. G. Makarov, A. V. Zibarev, B. A. Trofimov, L. N. Sobenina, K. V. Belyaeva, V. Ya. Sosnovskikh, D. L. Obydennov, S. A. Usachev, “Organofluorine chemistry: promising growth areas and challenges”, Russian Chem. Reviews, 88:5 (2019), 425–569  mathnet  mathnet  crossref  isi  scopus
    6. V. V. Astakhova, M. Yu. Moskalik, A. S. Ganin, B. A. Shainyan, “Reactions of N-Allyl- and N,N-Diallyltrifluoromethanesulfonamides with Carboxylic Acid Amides under Oxidizing Conditions”, Russ J Org Chem, 54:6 (2018), 855  crossref
    7. M. Yu. Moskalik, V. V. Astakhova, B. A. Shainyan, “Heterocyclization of carboxy- and sulfonamides in the course of oxidative addition to unsaturated substrates”, Russ Chem Bull, 66:12 (2017), 2212  crossref
    8. V. V. Astakhova, M. Yu. Moskalik, B. A. Shainyan, “Oxidative trifluoroacetamidation of (1E,3E)-1,4-diphenylbuta-1,3-diene and 1,1,4,4-tetraphenylbuta-1,3-diene”, Russ J Org Chem, 53:7 (2017), 981  crossref
    9. B. A. Shainyan, V. V. Astakhova, A. S. Ganin, M. Yu Moskalik, I. V. Sterkhova, “Oxidative addition/cycloaddition of arenesulfonamides and triflamide to N-allyltriflamide and N,N-diallyltriflamide”, RSC Adv., 7:62 (2017), 38951  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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