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Nucleophilic reactions of molybdenum cationic propargyl complexes

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Abstract

Reactions of molybdenum complexes with a η3-propargyl ligand with nucleophilic reagents (PPh3, PPh2H, Pr i2 NH, Py) were studied. These reactions were found to give two types of products: 1) mono- or dicationic complexes with a 2-substituted allylic ligand (PPh2H, Pr i2 NH, PPh3); 2) complexes with a η2-ammonio(phosphonio)allene ligand (Py, PPh3). The reactivity of molybdenum complexes was compared with that of Re, Pt, and Pd propargyl complexes, which revealed similarities and differences in their behavior depending on various factors. Molybdenum 1- and 2-phosphonioallyl complexes were obtained, the latter was studied by X-ray diffraction analysis.

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References

  1. B. M. Trost, T. R. Verhoven, in Comprehensive Organometallic Chemistry, Pergamon Press, Oxford, UK, 1982, Vol. 8, p. 799.

    Book  Google Scholar 

  2. M. Ephritikhine, B. R. Francis, M. L. H. Green, R. E. MacKenzie, M. Smith, J. Chem. Soc., Dalton Trans., 1977, 1131; DOI: https://doi.org/10.1039/DT97700011313.

  3. R. A. Periana, R. G. Bergman, J. Am. Chem. Soc., 1986, 108, 7346; DOI: https://doi.org/10.1021/ja00283a033.

    Article  CAS  Google Scholar 

  4. E. B. Tjaden, J. M. Stryker, Organometallics, 1992, 11, 16; DOI: https://doi.org/10.1021/om00037a009.

    Article  CAS  Google Scholar 

  5. L. S. Hegedus, W. H. Darlington, C. E. Russel, J. Org. Chem., 1980, 45, 5193; DOI: https://doi.org/10.1021/jo01313a034.

    Article  CAS  Google Scholar 

  6. C. Carfagna, R. Galarini, A. Musco, R. Santi, Organometallics, 1991, 10, 3956; DOI: https://doi.org/10.1021/om00058a005.

    Article  CAS  Google Scholar 

  7. C. Carfagna, R. Galarini, K. Linn, J. A. Lopez, C. Mealli, A. Musco, Organometallics, 1993, 12, 3019; DOI: https://doi.org/10.1021/om00032a026.

    Article  CAS  Google Scholar 

  8. S. G. Davies, M. L. H. Green, D. P. M. Mingos, Tetrahedron, 1978, 34, 3047; DOI:https://doi.org/10.1016/0040-4020(78)87001-X.

    Article  CAS  Google Scholar 

  9. J.-T. Chen, Coord. Chem. Rev., 1999, 190/192, 1143; DOI; https://doi.org/10.1016/S0010-8545(99)00180-0.

    Article  Google Scholar 

  10. V. V. Krivykh, E. S. Taits, P. V. Petrovskii, Organomet. Chem. USSR, 1989, 2, 492.

    Google Scholar 

  11. V. V. Krivykh, E. S. Taits, P. V. Petrovskii, Yu. T. Struchkov, A. I. Yanovsky, Mendeleev Commun., 1991, 1, 103; DOI: https://doi.org/10.1070/MC1991v001n03ABEH000063G.

    Article  Google Scholar 

  12. E. S. Taits, P. V. Petrovskii, V. V. Krivykh, Russ. Chem. Bull., 1999, 48, 1774; DOI: https://doi.org/10.1007/BF02494828.

    Article  CAS  Google Scholar 

  13. A. N. Nesmeyanov, V. V. Krivykh, E. S. Il’minskaya, M. I. Rybinskaya, J. Organomet. Chem., 1981, 209, 309; DOI: https://doi.org/10.1016/S0022-328X(00)81189-4.

    Article  CAS  Google Scholar 

  14. V. V. Krivykh, E. S. Taits, N. A. Shteltser, F. M. Dolgushin, J. Organomet. Chem., 2020, 913, 121201; DOI: https://doi.org/10.1016/j.jorganchem.2020.121201.

    Article  CAS  Google Scholar 

  15. V. V. Krivykh, Ph. D. Thesis (Chem.), 2012, p. 95 (in Russian).

  16. Y.-C. Cheng, Y.-K. Chen, T.-M. Huang, C.-I. Yu, G.-H. Lee, Y. Wang, J.-T. Chen, Organometallics, 1998, 17, 2953; DOI: https://doi.org/10.1021/om9708642.

    Article  CAS  Google Scholar 

  17. I. I. Kritskaya, Metody elementoorganicheskoy khimii, tipy metalloorganicheskikh compounds perekhodnykh metallov [Methods of Organoelement Chemistry, Types of Organometallic Compounds of Transition Metals], Ed. A. N. Nesmeyanov, Nauka, Moscow, 1975, Book 2, p. 749 (in Russian).

  18. V. V. Krivykh, O. V. Gusev, P. V. Petrovskii, M. I. Rybinskaya, J. Organomet. Chem., 1989, 366, 129; DOI: https://doi.org/10.1016/0022-328X(89)87322-X.

    Article  CAS  Google Scholar 

  19. M. Franck-Neumann, F. Brion, Angew. Chem., Int. Ed., Engl., 1979, 18, 688; DOI: https://doi.org/10.1002/anie.197906881.

    Article  Google Scholar 

  20. C. P. Casey, T. M. Boller, J. S. M. Samec, J. R. Reinert-Nash, Organometallics, 2009, 28, 123; DOI:https://doi.org/10.1021/om800739j.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. T.-M. Huang, J.-T. Chen, G.-H. Lee, Y. Wang, J. Am. Chem. Soc., 1993, 115, 1170; DOI https://doi.org/10.1021/ja00056a064.

    Article  CAS  Google Scholar 

  22. C. P. Casey, J. R. Nash, C. S. Yi, A. D. Selmeczy, S. Chung, D. R. Powell, R. K. Hayashi, J. Am. Chem. Soc., 1998, 120, 722; DOI: https://doi.org/10.1021/ja9729847.

    Article  CAS  Google Scholar 

  23. M. W. Baize, P. W. Blosser, V. Plantevin, D. G. Schimpff, J. C. Gallucci, A. Wojcicki, Organometallics, 1996, 15, 164; DOI: https://doi.org/10.1021/om9506678.

    Article  CAS  Google Scholar 

  24. A. Wojcicki, New J. Chem., 1994, 18, 61.

    CAS  Google Scholar 

  25. C. Carfagna, R. J. Deeth, M. Green, M. F. Mahon, J. M. McInnes, S. Pellegrini, C. B. Woolhouse, J. Chem. Soc., Dalton Trans., 1995, 3975; DOI: https://doi.org/10.1039/DT9950003975.

  26. P. W. Blosser, J. C. Gallucci, A. Wojcicki, J. Am. Chem. Soc., 1993, 115, 2994; DOI: https://doi.org/10.1021/ja00060a065.

    Article  CAS  Google Scholar 

  27. J. P. Graham, A. Wojcicki, B. E. Bursten, Organometallics, 1999, 18, 837; DOI:https://doi.org/10.1021/om9808209.

    Article  CAS  Google Scholar 

  28. H. Ohno, Chem. Pharm. Bull., 2005, 53, 1211; DOI: https://doi.org/10.1248/cpb.53.1211.

    Article  CAS  Google Scholar 

  29. H. Ohno, A. Okanao, S. Kosaka, K. Tsukamoto, M. Ohata, K. Ishihara, H. Maeda, T. Tanaka, N. Fujii, Org. Lett., 2008, 10, 1171; DOI: https://doi.org/10.1021/ol800063d.

    Article  CAS  PubMed  Google Scholar 

  30. M. Yoshida, T. Murao, K. Sugimoto, M. Ihara, Synlett, 2007, 575; DOI: https://doi.org/10.1055/s-2007-967962.

  31. G. M. Sheldrick, SADABS, 1997, Bruker AXS Inc., Madison, WI-53719, USA.

    Google Scholar 

  32. G. M. Sheldrick, Acta Cryst., 2015, C71, 3, DOI: https://doi.org/10.1107/S2053229614024218.

    Google Scholar 

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Build. 1, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    V. V. Krivykh & E. S. Taits

  2. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    F. M. Dolgushin

Authors
  1. V. V. Krivykh
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  2. E. S. Taits
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  3. F. M. Dolgushin
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Correspondence to V. V. Krivykh, E. S. Taits or F. M. Dolgushin.

Additional information

This work was carried out within the Russian State Assignment No. 075-00697-22-00 of the Ministry of Science and Higher Education of the Russian Federation using the equipment of the Center for Molecular Structure Studies at the A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.

X-ray diffraction study was carried out using the equipment of the Center for Collective Use of Physical Methods for the Study of Substances and Materials of the N. S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1139–1149, May, 2023.

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Krivykh, V.V., Taits, E.S. & Dolgushin, F.M. Nucleophilic reactions of molybdenum cationic propargyl complexes. Russ Chem Bull 72, 1139–1149 (2023). https://doi.org/10.1007/s11172-023-3882-2

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  • DOI: https://doi.org/10.1007/s11172-023-3882-2

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