LITHIUM DERIVATIVES OF 5-METHYL-5,10-DIHYDROINDENO[1,2-b] INDOLE AND 1,3,5-TRIMETHYL-6H- DIHYDROINDENO[2,1-b] INDOLE. SYNTHESIS AND MOLECULAR STRUCTURE

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The reaction of 1,3-dimethyl-5,6-dihydroindeno[2,1-b]indole with methyl iodide in the presence of cetyltrimethylammonium bromide yielded 1,3,5-trimethyl-6H-indeno[2,1-b]indole (L1H). The molecular structure of the compound was confirmed by X-ray diffraction. 1,3,5-Trimethyl-6H-indeno[2,1-b]indole (L1H) and 5-methyl-5,10-indeno[1,2-b]indole (L2H) are metallated with n-butyl lithium in diethyl ether at 0°C to form the corresponding lithium derivatives L1Li(Et2O)2 (1) and L2Li(Et2O)2 (2). According to X-ray diffraction data, lithium complex 2 has a monomeric structure, with two crystallographically independent molecules of the complex located in the independent region of the crystal cell. In molecule 2b, the lithium cation is coordinated by the five-membered ligand cycle by the η5-type, and in molecule 2a, by the η3-type.

About the authors

A. O Tolpygin

Razuvayev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: toao2@yandex.ru
ORCID iD: 0000-0002-3196-0229
Candidate of Chemical Sciences, Senior Researcher Nizhny Novgorod, Russian Federation

A. V Cherkasov

Razuvayev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: ach@iomc.ras.ru
ORCID iD: 0000-0001-8095-3562
Junior Researcher Nizhny Novgorod, Russian Federation

G. K Fukin

Razuvayev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: gera@iomc.ras.ru
ORCID iD: 0000-0002-1184-5418
Doctor of Chemical Sciences, Senior Researcher Nizhny Novgorod, Russian Federation

I. E Nifant'ev

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: inif@ips.ac.ru
ORCID iD: 0000-0001-9151-1890
Doctor of Chemical Sciences, Head of Laboratory Moscow, Russian Federation

A. A Trifonov

Razuvayev Institute of Organometallic Chemistry, Russian Academy of Sciences; Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Author for correspondence.
Email: trif@iomc.ras.ru
ORCID iD: 0000-0002-9072-4517
Doctor of Chemical Sciences, Corresponding Member of the Russian Academy of Sciences, Head of Laboratory Nizhny Novgorod, Russian Federation; Moscow, Russian Federation

References

  1. Kealy T.J., Pauson P.L. //Nature. 1951. V. 168. P. 1039. https://doi.org/10.1038/1681039b0
  2. Sapunov V.N., Kirchner K., Schmid R. //Coord. Chem. Rev. 2001. V. 214. P. 143. https://doi.org/10.1016/S0010-8545(00)00390-8
  3. Hierlmeier G., Wolf R. //Organometallics. 2022. V. 41. № 6. P. 776. https://doi.org/10.1021/acs.organomet.2c00009
  4. Wirtz L., Schafer A. //Chem. Eur. J. 2021. V. 27. P. 1219. https://doi.org/10.1002/chem.202003161
  5. Jutzi P., Burford N. //Chem. Rev. 1999. V. 99. № 4. P. 969. https://doi.org/10.1021/cr941099t.
  6. Lauk S., Schäfer Dr.A. //Eur. J. Inorg. Chem. 2021. V. 48. P. 5026. https://doi.org/10.1002/ejic.202100770
  7. Chirik P.J. //Organometallics. 2010. V. 29. P. 1500. https://doi.org/10.1021/om100016p.
  8. Coville N.J., du Plooy K.E., Pickl W. //Coord. Chem. Rev. 1992. V. 116. P. l. https://doi.org/10.1016/0010-8545(92)80070-8
  9. Deck P.A. //Coord. Chem. Rev. 2006. V. 250. P. 1032. https://doi.org/10.1016/j.ccr.2005.11.001
  10. Field L.D., Lindall C.M., Masters A.F., Clentsmith G.K.B. //Coord. Chem. Rev. 2011. V. 255. P. 1733. https://doi.org/10.1016/j.ccr.2011.02.001
  11. Arndt S., Okuda J. //Chem. Rev. 2002. V. 102. № 6. P. 195. https://doi.org/10.1021/cr010313s.
  12. Day B.M., Guo F.-S., Layfield R.A. //Acc. Chem. Res. 2018. V. 51. P. 1880. https://doi.org/10.1021/acs.accounts.8b00270
  13. Ephritikhine M. //Organometallics. 2013. V. 32. № 9. P. 2464. https://doi.org/10.1021/om400145p
  14. Arnold P.L., Dutkiewicz M.S., Walter O. //Chem. Rev. 2017. V. 117. P. 11460. https://doi.org/10.1021/acs.chemrev.7b00192
  15. Nifant’ev I.E., Ivchenko P.V., Vinogradov A.A. //Coord. Chem. Rev. 2021. V. 426. P. 213515. https://doi.org/10.1016/j.ccr.2020.213515
  16. Nifant’ev I.E., Vinogradov A.A., Vinogradov A.A. et al. //Appl. Catal. A. 2019. V. 571. P. 12. https://doi.org/10.1016/j.apcata.2018.12.006
  17. Grandini C., Camurati I., Guidotti S. et al. //Organometallics. 2004. V. 23. P. 344. https://doi.org/0.1021/om030543s
  18. De Rosa C., Auriemma F., Ruiz de Ballesteros O. //J. Am. Chem. Soc. 2003. V. 125, P. 10913. https://doi.org/10.1021/ja035911y
  19. Nifant’ev I.E., Bagrov V.V. Patent US6451724. 2002. https://patents.google.com/patent/US6451724B1
  20. Rigaku Oxford Diffraction. CrysAlis Pro Software System. Version 42.94a. Wroclaw (Poland): Rigaku Corporation, 2023.
  21. Sheldrick G.M. //Acta Crystallodr. C. 2015. V. 71. P. 3. https://doi.org/10.1107/S2053229614024218
  22. Sheldrick G.M. //Acta Crystallodr. A. 2015. V. 71. P. 3. https://doi.org/10.1107/S2053273314026370
  23. Li G., Wang E., Chen H. et al. //Tetrahedron. 2008. V. 64. P. 9033. https://doi.org/10.1016/j.tet.2008.07.021
  24. Feil F., Harder S. //Eur. J. Inorg. Chem. 2003. V. 18. P. 3401. https://doi.org/10.1002/ejic.200300149
  25. Michel R., Herbst-Irmer R., Stalke D. //Organometallics. 2011. V. 30. P. 4379. https://doi.org/10.1021/om200471e
  26. Tolpygin A.O., Cherkasov A.V., Fukin G.K. //Organometallics. 2025. V. 44. P. 158. https://doi.org/10.1021/acs.organomet.4c00416

Supplementary files

Supplementary Files
Action
1. JATS XML

Copyright (c) 2025 Russian Academy of Sciences

Согласие на обработку персональных данных

 

Используя сайт https://journals.rcsi.science, я (далее – «Пользователь» или «Субъект персональных данных») даю согласие на обработку персональных данных на этом сайте (текст Согласия) и на обработку персональных данных с помощью сервиса «Яндекс.Метрика» (текст Согласия).