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Reaction of benzyl phenyl ketazine with PCl3: synthesis of substituted 1,2,3-diazaphosphole and its reactions with strong nucleophiles and bases

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Abstract

The reaction of benzyl phenyl ketazine with PCl3 in tetrahydrofuran affords 2-(1,2-diphenylvinyl)-4,5-diphenyl-2H-[1,2,3]diazaphosphole (1). An unusual 1,3-addition of methyllithium at the nitrogen (N-Li) and phosphorus (P-Me) atoms of diazaphosphole was discovered. The reduction peak potentials of diazaphosphole (1) and the starting ketazine were measured by cyclic voltammetry.

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References

  1. Yu. S. Panova, A. V. Khristolyubova, V. V. Sushev, N. V. Zolotareva, M. D. Grishin, E. V. Baranov, G. K. Fukin, A. N. Kornev, Russ. Chem. Bull., 2021, 70, 1973; DOI: https://doi.org/10.1007/s11172-021-3305-1.

    Article  CAS  Google Scholar 

  2. A. N. Kornev, Y. S. Panova, V. V. Sushev, D. F. Dorado Daza, A. S. Novikov, A. V. Cherkasov, G. K. Fukin, G. A. Abakumov, Inorg Chem., 2019, 58, 16144; DOI: https://doi.org/10.1021/acs.inorgchem.9b02690.

    Article  CAS  PubMed  Google Scholar 

  3. A. N. Kornev, Yu. S. Panova, V. V. Sushchev, V. E. Galperin, A. V. Sheyanova, G. K. Fukin, E. V. Baranov, G. A. Abakumov, Russ. J. Coord. Chem., 2020, 46, 98; DOI: https://doi.org/10.1134/S1070328420020050.

    Article  CAS  Google Scholar 

  4. A. N. Kornev, V. V. Sushchev, N. V. Zolotareva, A. V. Arapova, V. E. Galperin, A. V. Cherkasov, G. A. Abakumov, Russ. Chem. Bull., 2015, 64, 228; DOI: https://doi.org/10.1007/s11172-015-0848-z.

    Article  CAS  Google Scholar 

  5. Yu. Panova, A. Khristolyubova, N. Zolotareva, V. Sushev, V. Galperin, R. Rumyantcev, G. Fukin, A. Kornev, Dalton Trans., 2021, 50, 5890; DOI: https://doi.org/10.1039/d1dt00747e.

    Article  CAS  PubMed  Google Scholar 

  6. A. N. Kornev, V. V. Sushchev, V. V. Kireeva, V. E. Galperin, N. V. Zolotareva, A. V. Cherkasov, G. A. Abakumov, Dokl. Chem., 2015, 462, 145; DOI: https://doi.org/10.1134/S0012500815060063.

    Article  CAS  Google Scholar 

  7. A. N. Kornev, V. E. Galperin, V. V. Sushev, N. V. Zolotareva, E. V. Baranov, G. K. Fukin, G. A. Abakumov, Eur. J. Inorg. Chem., 2016, 22, 3629; DOI: https://doi.org/10.1002/ejic.201600348.

    Article  Google Scholar 

  8. A. N. Kornev, V. E. Galperin, V. V. Sushev, Yu. S. Panova, G. K. Fukin, A. V. Cherkasov, G. A. Abakumov, Russ. Chem. Bull., 2016, 65, 2658; DOI: https://doi.org/10.1007/s11172-016-1632-4.

    Article  CAS  Google Scholar 

  9. A. N. Kornev, D. F. Dorado Daza, V. V. Sushev, Yu. S. Panova, V. E. Galperin, G. K. Fukin, E. V. Baranov, G. A. Abakumov, Russ. Chem. Bull., 2018, 67, 114; DOI: https://doi.org/10.1007/s11172-018-2045-3.

    Article  CAS  Google Scholar 

  10. A. N. Kornev, V. E. Galperin, V. V. Sushev, N. V. Zolotareva, G. K. Fukin, A. V. Cherkasov, G. A. Abakumov, Russ. Chem. Bull., 2016, 65, 2425; DOI: https://doi.org/10.1007/s11172-016-1601-y.

    Article  CAS  Google Scholar 

  11. A. N. Kornev, V. E. Galperin, Y. S. Panova, A. V. Arapova, E. V. Baranov, G. K. Fukin, G. A. Abakumov, Z. Anorg. Allg. Chem., 2017, 643, 1208; DOI: https://doi.org/10.1002/zaac.201700223.

    Article  CAS  Google Scholar 

  12. Y. S. Panova, V. V. Sushev, D. F. Doroado Daza, N. V. Zolotareva, R. V. Rumyantcev, G. K. Fukin, A. N. Kornev, Inorg. Chem., 2020, 59, 11337; DOI: https://doi.org/10.1021/acs.inorgchem.0c00913.

    Article  CAS  PubMed  Google Scholar 

  13. N. Gupta, Recent Advances in the Chemistry of Diazaphospholes, in Phosphorus Heterocycles II. Topics in Heterocyclic Chemistry, Ed. R. Bansal, Springer, Berlin, Heidelberg, 2010, Vol 21; DOI: https://doi.org/10.1007/7081_2009_20.

    Google Scholar 

  14. A. N. Kornev, N. V. Zolotareva, V. V. Sushev, A. V. Cherkasov, G. A. Abakumov, Mendeleev Commun., 2015, 25, 236; DOI: https://doi.org/10.1016/j.mencom.2015.05.028.

    Article  CAS  Google Scholar 

  15. V. A. Lopyrev, L. I. Larina, T. I. Vakul’skaya, Russ. Chem. Rev., 1986, 55, 411; DOI: https://doi.org/10.1070/rc1986v055n05abeh003198.

    Article  Google Scholar 

  16. J. Heinicke, K. Steinhauser, N. Peulecke, A. Spannenberg, P. Mayer, K. Karaghiosoff, Organometallics, 2002, 21, 912; DOI: https://doi.org/10.1021/om010884a.

    Article  CAS  Google Scholar 

  17. W. Rösch, M. Regitz, Phosphorus, Sulfur, Relat. Elem., 1984, 21, 97; DOI: https://doi.org/10.1080/03086648408073131.

    Article  Google Scholar 

  18. M. Ghalib, P. G. Jones, J. W. Heinicke, J. Organomet. Chem., 2014, 763–764, 44; DOI: https://doi.org/10.1016/j.jorganchem.2014.04.014.

    Article  Google Scholar 

  19. Y. Tamaru, T. Harada, Z. Yoshida, J. Org. Chem., 1978, 43, 3370; DOI: https://doi.org/10.1021/jo00411a023.

    Article  CAS  Google Scholar 

  20. A. N. Kornev, V. V. Sushev, N. V. Zolotareva, E. V. Baranov, G. K. Fukin, G. A. Abakumov, Org. Lett., 2015, 17, 6154; DOI: https://doi.org/10.1021/acs.orglett.5b02860.

    Article  CAS  PubMed  Google Scholar 

  21. Yu. S. Panova, A. V. Khristolyubova, V. V. Sushev, N. V. Zolotareva, E. V. Baranov, G. K. Fukin, A. N. Kornev, New J. Chem., 2021, 45, 18491; DOI: https://doi.org/10.1039/D1NJ03341G.

    Article  CAS  Google Scholar 

  22. Organic Solvents. Physical Properties and Methods of Purification, Ed. A. Weissberger, Interscience Publishers, Inc., New York, 1955.

    Google Scholar 

  23. J. Safari, S. Gandomi-Ravandi, RSC Adv., 2014, 4, 46224; DOI: https://doi.org/10.1039/C4RA04870A.

    Article  CAS  Google Scholar 

  24. Bruker, SAINT Data Reduction and Correction Program v.8.38A, Bruker AXS, Madison, Wisconsin, USA, 2017.

    Google Scholar 

  25. G. M. Sheldrick, Acta Cryst. A, 2015, 71, 3; DOI: https://doi.org/10.1107/S2053273314026370.

    Article  Google Scholar 

  26. G. M. Sheldrick, SHELXTL, Version 6.14. Structure Determination Software Suite, Bruker AXS, Madison, WI, USA, 2003.

    Google Scholar 

  27. G. M. Sheldrick, SADABS v.2016/2, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA, 2016.

    Google Scholar 

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Funding

The study was financially supported by the Russian Science Foundation (Project No. 19-13-00400-P) and performed using the equipment of the Center for Collective Use “Analytical Center of the IOMC RAS” with the financial support from the Ministry of Science and Higher Education of the Russian Federation (grant “Ensuring the Development of the Material and Technical Infrastructure of the Centers for Collective Use of Scientific Equipment,” agreement number 13.TsKP.21. 0017 (075-15-2021-670), RF 2296.61321X0017).

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Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603137, Nizhny Novgorod, Russia

    V. V. Sushev, N. V. Zolotareva, M. D. Grishin, Yu. S. Panova, A. V. Khristolyubova, E. V. Baranov, G. K. Fukin & A. N. Kornev

Authors
  1. V. V. Sushev
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  2. N. V. Zolotareva
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  3. M. D. Grishin
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  4. Yu. S. Panova
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  5. A. V. Khristolyubova
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  6. E. V. Baranov
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  7. G. K. Fukin
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  8. A. N. Kornev
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Corresponding author

Correspondence to A. N. Kornev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2273–2279, October, 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Sushev, V.V., Zolotareva, N.V., Grishin, M.D. et al. Reaction of benzyl phenyl ketazine with PCl3: synthesis of substituted 1,2,3-diazaphosphole and its reactions with strong nucleophiles and bases. Russ Chem Bull 71, 2272–2279 (2022). https://doi.org/10.1007/s11172-022-3655-3

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