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.
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:
Vera V. Astakhova, Mikhail Yu. Moskalik, Bagrat A. Shainyan, “Reactions of carboxamides with vinylsilanes under oxidative conditions”, Journal of Organometallic Chemistry, 960 (2022), 122230
Bagrat A. Shainyan, “N-Heterocycles via oxidative intramolecular cyclization”, Russian Chem. Reviews, 91:9 (2022), RCR5052
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
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
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
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
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
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
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