RAS Chemistry & Material ScienceКоординационная химия Russian Journal of Coordination Chemistry

  • ISSN (Print) 0132-344X
  • ISSN (Online) 3034-5499

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

PII
10.31857/S0132344X24080012-1
DOI
10.31857/S0132344X24080012
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 50 / Issue number 8
Pages
471-483
Abstract
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.
Keywords
гетероциклические соединения (арен)хромтрикарбонильные комплексы 1 3-бензодиоксан диастереомеры региоизомеры
Date of publication
15.08.2024
Year of publication
2024
Number of purchasers
0
Views
10

References

  1. 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. 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. 3. Pape A.R., Kaliappan K.P., Kündig E.P. // Chem. Rev. 2000. V. 100. P. 2917. https://doi.org/10.1021/cr9902852
  4. 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. 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. 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. 7. Rosillo M., Domínguez G, Pérez-Castells J. // Chem. Soc. Rev. 2007. V. 36. P. 1589. https://doi.org/10.1039/B606665H
  8. 8. Гришина Н.Ю., Сазонова Е.В., Артемов А.Н. // Журн. орган. химии. 2022. Т. 58. № 06. С. 555 (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. 9. Биометаллоорганическая химия / Под ред. Жауэна Ж. Москва: Бином, 2015. 505 с. (Bioorganometallics: Biomolecules, Labeling, Medicine. / Ed. Jaouen G. Weinheim: Willey-VCH, 2005. 444 p). https://doi.org/10.1002/3527607692
  10. 10. Baldoly C., Maiorana S., Licandro E. et al. // Org. Lett. 2002. V. 4. P. 4341. https://doi.org/10.1021/ol026994a
  11. 11. Baldoly C., Giannini C., Licandro E. et al. // Synlett. 2004. V. 6. P. 1044. https://doi.org/10.1055/s-2004-822886
  12. 12. Baldoly C., Cerea P., Giannini C. et al. // Synlett. 2005. V. 13. P. 1984. https://doi.org/10.1055/s-2005-871950
  13. 13. Varenne A., Vessières A., Brossier P., Jaouen G. // Res. Commun. Chem. Pathol. Pharmacol. 1994. V. 84. P. 81.
  14. 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. 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. 16. Ratni H., Kündig E.P. // Org. Lett. 1999. V. 1. P. 1997. https://doi.org/10.1021/ol991158v
  17. 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. 18. Kamikawa K., Tachibana A., Sugimoto S., Uemura M. // Org. Lett. 2001. V. 3. P. 2033. https://doi.org/10.1021/ol010076f
  19. 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. 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. 21. Uemura M., Daimon A., Hayashi Y. // Chem. Commun. 1995. P. 1943. https://doi.org/10.1039/C39950001943
  22. 22. Batuecas M., Luo J., Gergelitsová I. et al. // ACS Catal. 2019. V. 9. P. 5268. https://doi.org/10.1021/acscatal.9b00918
  23. 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. 24. Patent EP 0094738 B1. 1986.
  25. 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. 26. Сазонова Е. В., Артемов А.Н., Фаерман В.И. и др. // Изв. АН. Сер. хим. 2021. № 1. С. 171 (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. 27. Nikitin K., Bothe C., Müller-Bunz H. et al. // Organometallics. 2012. V. 31, P. 6183. https://dx.doi.org/10.1021/om300512z
  28. 28. Вайсбергер А., Проскауэр Э., Риддик Дж., Тупс Э. Органические растворители. Физические свойства и методы очистки. М.: ИЛ, 1958. 519 с. (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. 29. Huang L., Su T., Shan W. et al. // Bioorg. Med. Chem. 2012. V. 20. № 9. P. 3038. https://doi:10.1016/j.bmc.2012.02.059
  30. 30. Богомазова А.А., Кунакова Р.В., Злотский С.С. // Башкирский хим. журн. 2010. Т. 17. № 3. C. 19.
  31. 31. Choudhury P.K., Almena J., Foubelo F., Yus M. // Tetrahedron. 1997. V. 53. № 51. P. 17373. https://doi.org/10.1016/s0040-4020 (97)10161-2
  32. 32. Adams R., Fogler M.F., Kreger C.W. // J. Am. Chem. Soc. 1922. V. 44. № 5. P. 1126. https://doi:10.1021/ja01426a026
  33. 33. Drehfahl G., Horhold H.H., Kuhne K. // Chem. Ber. 1965. V. 98. P. 1826. https://doi.org/10.1002/cber.19650980622
  34. 34. Rausch M. D., Moser G. A., Zaiko E. S., Lipman A. L. // J. Organomet. Chem. 1970. V. 23. P. 185.
  35. 35. Sheldrick G.M. // Acta Crystallogr. C. 2015. V. 71. P. 3. https://doi.org/10.1107/S2053229614024218
  36. 36. Hübschle C. B., Sheldrick G. M., Dittrich B. // J. Appl. Cryst. 2011. V. 44. P. 1281. https://doi.org/10.1107/S0021889811043202
  37. 37. Busing W.R., Levy H.A. // Acta Crystallogr. A. 1957. V. 10. P. 180 https://doi.org/10.1107/S0365110X57000584
  38. 38. Clark R.C., Reid J.S. // Acta Crystallogr. A. 1995. V. 51. № 6. P. 887. https://doi.org/ 10.1107/S0108767395007367
  39. 39. Coutouli-Argyropoulou E., Trakossas S. // Tetrahedron. 2011. V. 67. P. 1915. https://doi.org/10.1016/j.tet.2011.01.020
  40. 40. Заровкина Н.Ю., Сазонова Е.В., Артемов А.Н., Фукин Г.К. // Изв. АН. Сер. хим. 2016. № 7. С. 1790 (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. 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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