Characteristic Features of the Synthesis of 2,1,3-Benzothiadiazole-Substituted 1,3-Iminophosphine and Platinum Complex of this Compound

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Аннотация

In an attempt to synthesize a new iminomethylphosphine, tBuC(Ph2P)=N-Btd (Btd = 2,1,3-benzothiadiazole) by a three-step procedure including (1) NH2-Btd + tBuC(=O)Cl → tBuC(=O)NH-Btd; (2) tBuC(=O)NH-Btd + SOCl2 → tBuC(Cl)=N-Btd; (3) tBuC(Cl)=N-Btd + Ph2PSiMe3 → tBuC(Ph2P)=N-Btd, it was found that the second step is accompanied by the chlorination of the carbocycle in the benzothiadiazole moiety. The reaction of the imidoyl chloride tBuC(Cl)=N-(7-Cl-Btd) formed in this reaction with Ph2PSiMe3 gave 1,3-iminomethylphosphine tBuC(Ph2P)=N-(7-Cl-Btd) (PC=N). The byproducts formed in this step include 1,3-aminomethylphosphine oxide tBuC{Ph2P(O)}NH-(7-Cl-Btd) (POCN) and (Ph2POx)2,, resulting from partial oxidation and hydrolysis. The reactions of PC=N and POCN with [Pt(COD)Cl2] (COD = 1.3-cyclooctadiene) were studied. In the case of PC=N, the reaction affords the [Pt(PC=N)2Cl2] complex. In the latter case, cleavage of the P–C bond in POCN takes place, and [PtCl2(Ph2POH)2](POCN) and [Pt(CH3CN){tBuC-NH-(7-Cl-Btd)}Cl]. are isolated from the reaction mixture. The structures of the new compounds were established by single-crystal X-ray diffraction (tBuC(Cl)N-(7-Cl-Btd)), 2335152 (POCN · Et2O), 2335149 (Ph2POx)2, 2335153 ([Pt(PC=N)2Cl2]), 2335154 ([PtCl2(Ph2POH)2](POCN)), 2335151 ([Pt(CH3CN)(tBuC-NH-(7-Cl-Вbtd))Cl]).

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Авторлар туралы

R. Khisamov

Nikolaev Institute of Inorganic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: sukhikh@niic.nsc.ru
Ресей, Novosibirsk

S. Konchenko

Nikolaev Institute of Inorganic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: sukhikh@niic.nsc.ru
Ресей, Novosibirsk

T. Sukhikh

Nikolaev Institute of Inorganic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Хат алмасуға жауапты Автор.
Email: sukhikh@niic.nsc.ru
Ресей, Novosibirsk

Әдебиет тізімі

  1. Bálint E., Tajti Á., Tripolszky A., Keglevich G. // Dalton Trans. 2018. V. 47. P. 4755.
  2. Smith M.B. // Molecules. 2022. V. 27. P. 6293.
  3. Sukhikh T.S., Khisamov R.M., Konchenko S.N. // Symmetry. 2023. V. 15. P. 157.
  4. Khisamov R.M., Sukhikh T.S., Konchenko S.N., Pushkarevsky N.A. // Inorganics. 2022. V. 10. P. 263.
  5. Khisamov R.M., Ryadun A.A., Konchenko S.N., Sukhikh T.S. // Molecules. 2022. V. 27. P. 8162.
  6. Baranov A.Y., Sukhikh T.S., Artem′ev A.V. // J. Struct. Chem. 2022. V. 63. P. 658.
  7. Rogovoy M.I., Bagryanskaya I.Y., Sadykov E.H. // J. Struct. Chem. 2023. V. 64. P. 1654.
  8. Rong M.K., Holtrop F., Slootweg J.C., Lammertsma K. // Coord. Chem. Rev. 2019. V. 380. P. 1.
  9. Huber T., Bauer J.O. // Chem. Eur. J. 2023. P. e202303760.
  10. Farkas G., Császár Z., Tóth-Farsang E. et al. // J. Organomet. Chem. 2023. V. 994. P. 122723.
  11. Liu R., Liu Y., Yang W., Li X., Feng L. // ACS Omega. 2023. V. 8. P. 18290.
  12. Reis Conceição N., Mahmoud A.G., Guedes da Silva M.F.C. et al. // Mol. Catal. 2023. V. 549. P. 113512.
  13. Radcliffe J.E., Batsanov A.S., Smith D.M., Scott J.A. et al. // ACS Catalysis. 2015. V. 5. P. 7095.
  14. van Dijk T., Burck S., Rong M.K. et al. // Angew. Chem. Int. Ed. 2014. V. 53. P. 9068.
  15. Rong M.K., van Duin K., van Dijk T. et al. // Organometallics. 2017. V. 36. P. 1079.
  16. Kandel R., Huynh K., Dalgliesh L. et al. // Inorg. Chim. Acta. 2016. V. 445. P. 117.
  17. Lee K.-F., Yang T., Tsang L.-Y. et al. // Organometallics. 2021. V. 40. P. 358.
  18. Kandel R., Schatte G., Jessop P.G. // Dalton Trans. 2019. V. 48. P. 12512.
  19. Fischer M., Steinert H., Schmidtmann M., Beckhaus R. // Dalton Trans. 2019. V. 48. P. 1936.
  20. Sheldrick G. // Acta Crystallogr. A. 2015. V. 71. P. 3.
  21. Sheldrick G. // Acta Crystallogr. 2015. V. 71. P. 3.
  22. Dolomanov O.V., Bourhis L.J., Gildea R.J. et al. // J. Appl. Crystallogr. 2009. V. 42. P. 339.
  23. Alexeev A.V., Gromilov S.A. // J. Struct. Chem. 2010. V. 51. P. 156.
  24. Alexeev A.V., Gromilov S.A. // J. Struct. Chem. 2010. V. 51. P. 744.
  25. Prescher C., Prakapenka V.B. // High Pressure Res. 2015. V. 35. P. 223.
  26. Afonin M.Y., Martynenko P.A., Kolybalov D.S. // Inorg. Chem. 2024. V. 63. P. 369.
  27. Sukhikh T.S., Kolybalov D.S., Khisamov R.M., Konchenko S.N. // J. Struct. Chem. 2022. V. 63. P. 1446.
  28. Nieger M., Schinkels B., Niecke E. // Experimental Crystal Structure Determination. CCDC 174103. 2002. https://doi.org/10.5517/cc5v57d
  29. Dashti-Mommertz A., Neumüller B. // Z. Anorg. Allg. Chem. 1999. V. 625. P. 954.
  30. Tam E.C.Y., Maynard N.A., Apperley D.C. // Inorg. Chem. 2012. V. 51. P. 9403.
  31. Khisamov R.M., Konchenko S.N., Sukhikh T.S. // J. Struct. Chem. 2022. V. 63. P. 2113.
  32. Hu C., Wang M., Han X., Fan J. // J. Phys. Chem. C. 2021. V. 125. P. 22346.
  33. Khisamov R.M., Ryadun A.A., Konchenko S.N., Sukhikh T.S. // Molecules. 2022. V. 27. P. 3857.

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2. Scheme 1. General approaches to the synthesis of 1,3-iminomethylphosphines

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3. Fig. 1. Experimental (exp.) and simulated (sim.) powder diffractograms for [PtCl2(PC=N)2] (MoKα radiation)

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4. Scheme 2. Synthesis of 1,3-iminomethylphosphine PC=N

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5. Scheme 3. Side reaction of the formation of 1,3-aminomethylphosphinoxide POCN in the presence of air

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6. Scheme 4. Reactions of iminomethylphosphine PC=N and aminomethylphosphines PCN-Pbt [26] and POCN with [Pt(COD)Cl2]

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7. Fig. 2. Structure of the disordered molecule (Ph2POx)2, H atoms are not shown. The major position is shown in colour, the minor position in black. Populations of P and O atoms are indicated

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8. Fig. 3. Structure of a single molecule of 1,3-aminomethylphosphine in POCN - 0.5Et2O (a) and a pair of molecules with contact between (C)H and O atoms (b; other H atoms not shown)

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9. Fig. 4. Structure of [PtCl2(Ph2POH)2](POCN) (a); H atoms except those involved in hydrogen bonding are not shown, and [Pt(PC=N)2Cl2] (b), H atoms are not shown

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10. Fig. 5. Structure of [Pt(CH3CN){tBuC-NH-(7-Cl-Btd)}Cl] (a) and tBuC(Cl)=N-(7-Cl-Btd) (b)

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