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Triflamidation of Camphene in Nitrile Solutions
- Authors: Sobyanina M.M.1, Garagan I.A.1, Ganin A.S.1
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Affiliations:
- Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
- Issue: Vol 60, No 8 (2024)
- Pages: 15-22
- Section: Articles
- URL: https://aspvestnik.ru/0514-7492/article/view/676674
- DOI: https://doi.org/10.31857/S0514749224080028
- EDN: https://elibrary.ru/RBFCFX
- ID: 676674
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Abstract
The reaction of triflamide with camphene in nitrile solutions in the presence of NBS and NIS has been researched. The reactions in isobutyronitrile solution give of various products: dibromide, camphenol, bromamidation product and corresponding amidines. In the reaction in benzonitrile with NBS, two isomeric benzamidines were obtained and isolated. One of them is the product of rearrangement of the camphene framework during the reaction, while in the second one the original substrate structure is retained. When using NIS as an oxidizing agent in the same solvent, a similar mixture of isomers having an iodine atom was obtained.
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About the authors
M. M. Sobyanina
Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
Email: ganin@irioch.irk.ru
ORCID iD: 0000-0002-0361-0897
Russian Federation, Irkutsk
I. A. Garagan
Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
Email: ganin@irioch.irk.ru
ORCID iD: 0000-0003-3024-798X
Russian Federation, Irkutsk
A. S. Ganin
Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
Author for correspondence.
Email: ganin@irioch.irk.ru
ORCID iD: 0000-0003-1626-795X
Russian Federation, Irkutsk
References
- Zhou L., Zhou J., Tan C. K., Chen J., Yeung Y.-Y. Org. Lett. 2011, 13, 2448–2451. doi: 10.1021/ol2006902
- Ishikawa T. Superbases for Organic Synthesis. 2009. doi: 10.1002/9780470740859
- Berlinck R.G.S., Burtoloso A.C.B., Kossuga M.H. Nat. Prod. Rep. 2008, 919–954. doi: 10.1039/B507874C
- Berlinck R.G.S., Kossuga M.H. Nat. Prod. Rep. 2005, 22, 516–550. doi: 10.1039/B209227C
- Nagasawa K., Hashimoto Y. Chem. Rec. 2003, 3, 201–211. doi: 10.1002/tcr.10064
- Bellina F., Cauteruccio S., Rossi R. Tetrahedron. 2007, 63, 4571–4624. doi: 10.1016/j.tet.2007.02.075
- Luca L.D. Curr. Med. Chem. 2006, 13, 1–23. doi: 10.2174/092986706775197971
- Ahmad S.M., Braddock D.C., Cansell G., Hermitage S.A., Redmond J.M., White A.J.P. Tetrahedron Lett. 2007, 48, 5948–5952. doi: 10.1016/j.tetlet.2007.06.112
- Edelmann F.T., Hill A.F., Fink M.J. Advances in Physical Organic Chemistry. 2008, 183–352.
- Ganesh V., Sureshkumar D., Chanda D., Chandrasekaran S. Chem. Eur. J. 2012, 18, 12498–12511. doi: 10.1002/chem.201103556
- Moskalik M.Yu., Shainyan B.A., Ushakov I.A., Sterkhova I.V., Astakhova V.V. Tetrahedron. 2020, 76, 131018. doi: 10.1016/j.tet.2020.131018
- Garagan I.A., Moskalik M.Yu., Sterkhova I.V., Ganin A.S. Molbank 2023, 2023(2), M1645. doi: 10.3390/M1645
- Dağalan Z., Koçak R., Daştan A., Nişancı B. Org. Lett. 2022, 24, 8261–8264. doi: 10.1021/acs.orglett.2c02627
- Darby N., Lamb N., Money T. Can. J. Chem. 1979, 57, 742–746. doi: 10.1139/v79-121
- Ganin A.S, Sobyanina M.M, Moskalik M.Yu., Shainyan B.A. Russ. J. Org. Chem. 2023, 59, 1410–1417. doi.org/10.31857/S0514749223110022
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