Synthesis of (η6-Arene)tricarbonylchromium Complexes of 1,3-Benzodioxanes

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Resumo

The reactions of triamminotricarbonylchromium (I) with 1,3-benzodioxane (L1), 2-methyl-1,3-benzodioxane (L2), and 2-phenyl-1,3-benzodioxane (L3) afford new complexes: (η6-C8H8O2)Cr(CO)3 (II), exo- and endo-[2-Me-(η6-C8H7O2)]Cr(CO)3 (III, IV), exo- and endo-[2-Ph-(η6-C8H7O2)]Cr(CO)3 (V, VI), [2-(η6-Ph)-C8H7O2]Cr(CO)3 (VII), and endo-[2-(η6-Ph)]Cr(CO)3-[η6-C8H7O2]Cr(CO)3 (VIII). The structures, compositions, and purity of the synthesized products are proved by UV, IR, and 1H NMR spectroscopy, HPLC, and mass spectrometry. The molecular structures of complexes IV–VI are determined by XRD (CIF files CCDC nos. 2263301 (IV), 2295552 (V), and 2237106 (VI)). A possibility of coordination of the tricarbonylchromium group at different sides of the phenylene ring of ligands L2 and L3 and on the phenyl substituent of ligand L3 is shown.

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Sobre autores

N. Grishina

Lobachevsky National Research State University

Autor responsável pela correspondência
Email: zarovkinan@mail.ru
Rússia, Nizhny Novgorod

E. Sazonova

Lobachevsky National Research State University

Email: zarovkinan@mail.ru
Rússia, Nizhny Novgorod

P. Ushakova

Lobachevsky National Research State University

Email: zarovkinan@mail.ru
Rússia, Nizhny Novgorod

N. Somov

Lobachevsky National Research State University

Email: zarovkinan@mail.ru
Rússia, Nizhny Novgorod

E. Medvedeva

Lobachevsky National Research State University

Email: zarovkinan@mail.ru
Rússia, Nizhny Novgorod

A. Shishkin

Lobachevsky National Research State University

Email: zarovkinan@mail.ru
Rússia, Nizhny Novgorod

A. Artemov

Lobachevsky National Research State University

Email: zarovkinan@mail.ru
Rússia, Nizhny Novgorod

Bibliografia

  1. Transition Metal Arene π-Complexes in Organic Synthesis and Catalysts / Ed. Kündig E.P. Berlin: Springer-Verlag, 2004. V. 7. 232 p. https://doi.org/10.1007/b76615
  2. Schmalz H.-G., Dehmel F. Transition Metals for Organic Synthesis. / Eds. Beller M., Bolm C. Weinheim: Wiley-VCH, 2004. V. 1. P. 601. https://doi.org/10.1002/9783527619405
  3. Pape A.R., Kaliappan K.P., Kündig E.P. // Chem. Rev. 2000. V. 100. P. 2917. https://doi.org/10.1021/cr9902852
  4. Davies S.G., McCarthy T.D. Comprehensive Organometallic Chemistry II / Eds. Abel E.W., Stone F.G.A., Wilkinson G. Oxford: Pergamon, 1995. P. 1039. https://doi.org/10.1016/B978-008046519-7.00135-0
  5. Semmelhack M.F. Comprehensive Organometallic Chemistry II. / Eds. Abel E.W., Stone F.G.A., Wilikinson G. Oxford: Pergamon, 1995. V. 12. P. 979. https://doi.org/10.1016/B978-008046519-7.00133-7
  6. Semmelhack M.F. Comprehensive Organometallic Chemistry II / Eds. Abel E.W., Stone F.G.A., Wilikinson G. Oxford: Pergamon, 1995. V. 12. P. 1017. https://doi.org/10.1016/B978-008046519-7.00134-9
  7. Rosillo M., Domínguez G, Pérez-Castells J. // Chem. Soc. Rev. 2007. V. 36. P. 1589. https://doi.org/10.1039/B606665H
  8. Grishina N.Yu., Sazonova E.V., Artemov A.N. // Russ. J. Org. Chem. 2022. V 58. № 06. P. 727. https://doi.org/10.1134/S107042802206001X
  9. Bioorganometallics: Biomolecules, Labeling, Medicine. / Ed. Jaouen G. Weinheim: Willey-VCH, 2005. 444 p. https://doi.org/10.1002/3527607692
  10. Baldoly C., Maiorana S., Licandro E. et al. // Org. Lett. 2002. V. 4. P. 4341. https://doi.org/10.1021/ol026994a
  11. Baldoly C., Giannini C., Licandro E. et al. // Synlett. 2004. V. 6. P. 1044. https://doi.org/10.1055/s-2004-822886
  12. Baldoly C., Cerea P., Giannini C. et al. // Synlett. 2005. V. 13. P. 1984. https://doi.org/10.1055/s-2005-871950
  13. Varenne A., Vessières A., Brossier P., Jaouen G. // Res. Commun. Chem. Pathol. Pharmacol. 1994. V. 84. P. 81.
  14. Solladié-Cavallo A., Quazzotti S., Colonna S. et al. // Tetrahedron: Asymmetry. 1992. V. 3. P. 287. https://doi.org/10.1016/S0957-4166(00)80208-6
  15. Colonna S., Manfredi A., Solladié-Cavallo A. , Quazzotti S. // Tetrahedron Lett. 1990. V. 31. P. 6185. https://doi.org/10.1016/S0040-4039(00)97020-5
  16. Ratni H., Kündig E.P. // Org. Lett. 1999. V. 1. P. 1997. https://doi.org/10.1021/ol991158v
  17. Semmelhack M.F., Knochel P., Singleton T. // Tetrahedron Lett. 1993. V. 34. P. 5051. https://doi.org/10.1016/S0040-4039(00)60673-1
  18. Kamikawa K., Tachibana A., Sugimoto S., Uemura M. // Org. Lett. 2001. V. 3. P. 2033. https://doi.org/10.1021/ol010076f
  19. Patra M., Ingram K., Pierroz V et al. // Chem. Eur. J. 2013. V. 19. P. 2232. https://doi.org/10.1002/chem.201204291
  20. Kamikawa K., Watanabe T., Daimon A., Uemura M. // Tetrahedron. 2000. V. 56. P. 2325. https://doi.org/10.1016/S0040-4020(99)01115-1
  21. Uemura M., Daimon A., Hayashi Y. // Chem. Commun. 1995. P. 1943. https://doi.org/10.1039/C39950001943
  22. Batuecas M., Luo J., Gergelitsová I. et al. // ACS Catal. 2019. V. 9. P. 5268. https://doi.org/10.1021/acscatal.9b00918
  23. Han J.W., Son S. Uk, Chung Y.K. // J. Org. Chem. 1997. V. 62. P. 8264. https://doi.org/10.1021/jo9712761
  24. Patent EP 0094738 B1. 1986.
  25. Shah S.U.A., Ashraf N., Soomro Z.H. et al. // Inflammation Res. 2012 V. 61. P. 875. https://doi.org/10.1007/s00011-012-0480-4
  26. Sazonova E.V., Artemov A.N., Faerman V.I. et al. // Russ. Chem. Bull. (Int. Ed.) 2021. V. 70. № 1. P. 171. https://doi.org/10.1007/s11172-021-3073-y
  27. Nikitin K., Bothe C., Müller-Bunz H. et al. // Organometallics. 2012. V. 31, P. 6183. https://dx.doi.org/10.1021/om300512z
  28. Weissberger A., Proskauer E., Riddick J.A., Toops E.E. Jr. Organic Solvents; Physical Properties and Methods of Purification, Intersci. New York–London: Publ. Inc., 1955. 552 p.
  29. Huang L., Su T., Shan W. et al. // Bioorg. Med. Chem. 2012. V. 20. № 9. P. 3038. 10.1016/j.bmc.2012.02.059' target='_blank'>https://doi: 10.1016/j.bmc.2012.02.059
  30. Bogomazova, A.A., Kunakova, R.V., and Zlotskii S.S., Bashkirskii Khim. Zh., 2010, vol. 17, no. 3, p. 19.
  31. Choudhury P.K., Almena J., Foubelo F., Yus M. // Tetrahedron. 1997. V. 53. № 51. P. 17373. doi: 10.1016/s0040-4020(97)10161-2
  32. Adams R., Fogler M.F., Kreger C.W. // J. Am. Chem. Soc. 1922. V. 44. № 5. P. 1126. 10.1021/ja01426a026' target='_blank'>https://doi: 10.1021/ja01426a026
  33. Drehfahl G., Horhold H.H., Kuhne K. // Chem. Ber. 1965. V. 98. P. 1826. https://doi.org/10.1002/cber.19650980622
  34. Rausch M. D., Moser G. A., Zaiko E. S., Lipman A. L. // J. Organomet. Chem. 1970. V. 23. P. 185.
  35. Sheldrick G.M. // Acta Crystallogr. C. 2015. V. 71. P. 3. https://doi.org/10.1107/S2053229614024218
  36. Hübschle C. B., Sheldrick G. M., Dittrich B. // J. Appl. Cryst. 2011. V. 44. P. 1281. https://doi.org/10.1107/S0021889811043202
  37. Busing W.R., Levy H.A. // Acta Crystallogr. A. 1957. V. 10. P. 180 https://doi.org/10.1107/S0365110X57000584
  38. Clark R.C., Reid J.S. // Acta Crystallogr. A. 1995. V. 51. № 6. P. 887. doi: 10.1107/S0108767395007367
  39. Coutouli-Argyropoulou E., Trakossas S. // Tetrahedron. 2011. V. 67. P. 1915. https://doi.org/10.1016/j.tet.2011.01.020
  40. Zarovkina N.Yu., Sazonova E.V., Artemov A.N., Fukin G.K. // Russ. Chem. Bull. (Int. Ed.) 2016. V. 65. № 7. P. 1790. https://doi.org/10.1007/s11172-016-1512-y
  41. Karimi-Jaberi Z., Amiri M. // E.-J. Chem. 2012. V. № 1. P. 167. https://doi.org/10.1155/2012/793978

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2. Scheme 1

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3. Fig. 1. Molecular structure of endo-2-methyl-(η61,3-benzodioxane)chromotricarbonyl (IV)

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4. Fig. 2. PMR spectrum of the mixture of complexes V and VII

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5. Scheme 2

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6. Fig. 3. Molecular structure of exo-2-phenyl-(η61,3-benzodioxane)chromotricarbonyl (V)

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7. Fig. 4. Molecular structure of endo-2-phenyl-(η61,3-benzodioxane)chromotricarbonyl (VI)

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