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Alkali metal polyphosphides as intermediates in the synthesis of organophosphorus compounds from elemental phosphorus

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Abstract

Methods for the preparation of alkali metal polyphosphides, as well as their reactivity with respect to organic substrates, namely, electrophilic reagents and unsaturated compounds, were considered.

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References

  1. V. A. Miluykov, Yu. H. Budnikova, O. G. Sinyashin, Russ. Chem. Rev., 2005, 74, 781; DOI: https://doi.org/10.1070/RC2005v074n09ABEH001182.

    Article  CAS  Google Scholar 

  2. R. S. P. Turbervill, J. M. Goicoechea, Chem. Rev., 2014, 114, 10807; DOI: https://doi.org/10.1021/cr500387w.

    Article  CAS  PubMed  Google Scholar 

  3. N. K. Gusarova, B. A. Trofimov, Russ. Chem. Rev., 2020, 89, 225; DOI: https://doi.org/10.1070/RCR4903.

    Article  CAS  Google Scholar 

  4. M. Scheer, G. Balázs, A. Seitz, Chem. Rev., 2010, 110, 4236; DOI: https://doi.org/10.1021/cr100010e.

    Article  CAS  PubMed  Google Scholar 

  5. J. E. Borger, A. W. Ehlers, J. C. Slootweg, K. Lammertsma, Chem. Eur. J., 2017, 23, 11738; DOI: https://doi.org/10.1002/chem.201702067.

    Article  CAS  PubMed  Google Scholar 

  6. B. van Ijzendoorn, M. Mehta, Dalton Trans., 2020, 49, 14758; DOI: https://doi.org/10.1039/D0DT02890H.

    Article  CAS  PubMed  Google Scholar 

  7. Yu. H. Budnikova, D. G. Yakhvarov, O. G. Sinyashin, J. Organomet. Chem., 2005, 690, 2416; DOI: https://doi.org/10.1016/j.jorganchem.2004.11.008.

    Article  CAS  Google Scholar 

  8. D. G. Yakhvarov, E. V. Gorbachuk, O. G. Sinyashin, Eur. J. Inorg. Chem., 2013, 27, 4709; DOI: https://doi.org/10.1002/ejic.201300845.

    Article  CAS  Google Scholar 

  9. J. W. Dube, C. M. E. Graham, C. L. B. Macdonald, Z. D. Brown, P. P. Power, P. J. Ragogna, Chem. Eur. J., 2014, 20, 6739; DOI: https://doi.org/10.1002/chem.201402031.

    Article  CAS  PubMed  Google Scholar 

  10. D. Tofan, C. C. Cummins, Angew. Chem., Int. Ed., 2010, 49, 7516; DOI: https://doi.org/10.1002/anie.201004385.

    Article  CAS  Google Scholar 

  11. P. B. Arockiam, U. Lennert, C. Graf, R. Rothfelder, D. J. Scott, T. G. Fischer, K. Zeitler, R. Wolf, Chem. Eur. J., 2020, 26, 16374; DOI: https://doi.org/10.1002/chem.202002646.

    Article  CAS  PubMed  Google Scholar 

  12. M. Caporali, L. Gonsalvi, A. Rossin, M. Peruzzini, Chem. Rev., 2010, 110, 4178; DOI: https://doi.org/10.1021/cr900349u.

    Article  CAS  PubMed  Google Scholar 

  13. C. M. Hoidn, D. J. Scott, R. Wolf, Chem. Eur. J., 2021, 27, 1886; DOI: https://doi.org/10.1002/chem.202001854.

    Article  CAS  PubMed  Google Scholar 

  14. S. Yao, N. Lindenmaier, Y. Xiong, S. Inoue, T. Szilvási, M. Adelhardt, J. Sutter, K. Meyer, M. Driess, Angew. Chem., Int. Ed., 2015, 54, 1250; DOI: https://doi.org/10.1002/anie.201409469.

    Article  CAS  Google Scholar 

  15. F. Spitzer, C. Graßl, G. Balázs, E. M. Zolnhofer, K. Meyer, M. Scheer, Angew. Chem., Int. Ed., 2016, 55, 4340; DOI: https://doi.org/10.1002/anie.201510716.

    Article  CAS  Google Scholar 

  16. M. Ehses, A. Romerosa, M. Peruzzini, Top. Curr. Chem., 2002, 220, 107; DOI: https://doi.org/10.1007/3-540-45731-3_5.

    Article  CAS  Google Scholar 

  17. E. Fluck, C. M. E. Pavlidou, R. Janoschek, Phosphorus, Sulfur, Rel. Elem., 1979, 6, 469; DOI: https://doi.org/10.1080/03086647908069907.

    Article  CAS  Google Scholar 

  18. C. Brown, R. F. Hudson, G. A. Wartew, H. Coates, J. Chem. Soc., Chem. Commun., 1978, 1, 7; DOI: https://doi.org/10.1039/C39780000007.

    Article  Google Scholar 

  19. M. Baudler, C. Adamek, S. Opiela, H. Budzikiewicz, D. Ouzounis, Angew. Chem., 1988, 100, 1110; DOI: https://doi.org/10.1002/ange.19881000817.

    Article  CAS  Google Scholar 

  20. F. Kraus, J. C. Aschenbrenner, N. Korber, Angew. Chem., 2003, 115, 4162; DOI: https://doi.org/10.1002/ange.200351776.

    Article  Google Scholar 

  21. F. Kraus, T. Hanauer, N. Korber, Inorg. Chem., 2006, 45, 1117; DOI: https://doi.org/10.1021/ic0514445.

    Article  CAS  PubMed  Google Scholar 

  22. M. Baudler, T. Etzbach, Chem. Ber., 1991, 124, 1159; DOI: https://doi.org/10.1002/cber.19911240528.

    Article  CAS  Google Scholar 

  23. W. Hoenle, H.-G. von Schering, A. Schmidpeter, G. Burget, Angew. Chem., 1984, 96, 796; DOI: https://doi.org/10.1002/ange.19840961016.

    Article  CAS  Google Scholar 

  24. M. M. Shatruk, K. A. Kovnir, A. V. Shevelkov, B. A. Popovkin, Angew. Chem., 2000, 112, 2561; DOI: https://doi.org/10.1002/1521-3757(20000717)112:14<2561::AID-ANGE2561>3.0.CO;2-B.

    Article  Google Scholar 

  25. S. Lange, C. P. Sebastian, L. Zhang, H. Eckert, T. Nilges, Inorg. Chem., 2006, 45, 5878; DOI: https://doi.org/10.1021/ic060380a.

    Article  CAS  PubMed  Google Scholar 

  26. F. Guerin, D. Richeson, Inorg. Chem., 1995, 34, 2793; DOI: https://doi.org/10.1021/ic00115a002.

    Article  CAS  Google Scholar 

  27. V. A. Miluykov, A. V. Kataev, O. G. Sinyashin, E. Hey-Hawkins, Russ. Chem. Bull., 2006, 55, 1297; DOI: https://doi.org/10.1007/s11172-006-0414-9.

    Article  CAS  Google Scholar 

  28. A. Dragulescu-Andrasi, L. Z. Miller, B. Chen, D. T. McQuade, M. Shatruk, Angew. Chem., Int. Ed., 2016, 55, 3904; DOI: https://doi.org/10.1002/anie.201511186.

    Article  CAS  Google Scholar 

  29. V. Miluykov, A. Kataev, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Anorg. Allg. Chem., 2006, 632, 1728; DOI: https://doi.org/10.1002/zaac.200600108.

    Article  CAS  Google Scholar 

  30. M. Jo, A. Dragulescu-Andrasi, L. Z. Miller, C. Pak, M. Shatruk, Inorg. Chem., 2020, 59, 5483; DOI: https://doi.org/10.1021/acs.inorgchem.0c00108.

    Article  CAS  PubMed  Google Scholar 

  31. M. Baudler, S. Akpapoglou, D. Ouzounis, F. Wasgestian, B. Meinigke, H. Budzikiewicz, H. Münster, Angew. Chem., Int. Ed. Engl., 1988, 27, 280; DOI: https://doi.org/10.1002/anie.198802801.

    Article  Google Scholar 

  32. G. Fritz, H. Rothmann, E. Matern, Z. Anorg. Allg. Chem., 1992, 610, 33; DOI: https://doi.org/10.1002/zaac.19926100107.

    Article  CAS  Google Scholar 

  33. S. Charles, J. C. Fettinger, B. W. Eichhorn, J. Am. Chem. Soc., 1995, 117, 5303; DOI: https://doi.org/10.1021/ja00124a013.

    Article  CAS  Google Scholar 

  34. S. P. Mattamana, K. Promprai, J. C. Fettinger, B. W. Eichhorn, Inorg. Chem., 1998, 37, 6222; DOI: https://doi.org/10.1021/ic9804770.

    Article  CAS  Google Scholar 

  35. G. Fritz, E. Layher, D. Hanke, C. Persau, Z. Anorg. Allg. Chem., 1991, 594, 36; DOI: https://doi.org/10.1002/zaac.19915940105.

    Article  CAS  Google Scholar 

  36. V. A. Miluykov, A. V. Kataev, O. G. Sinyashin, E. Hey-Hawkins, Russ. Chem. Bull., 2007, 56, 298; DOI: https://doi.org/10.1007/s11172-007-0048-6.

    Article  CAS  Google Scholar 

  37. V. A. Miluykov, O. G. Sinyashin, A. V. Kataev, E. Hey-Hawkins, Phosphorus, Sulfur, Silicon, Rel. Elem., 2008, 183, 509; DOI: https://doi.org/10.1080/10426500701761623.

    Article  CAS  Google Scholar 

  38. M. Baudler, R. Becher, Z. Naturforsch. B, 1985, 40, 1090; DOI: https://doi.org/10.1515/znb-1985-0818.

    Article  Google Scholar 

  39. M. Baudler, R. Becher, J. Germeshausen, Chem. Ber., 1986, 119, 2510; DOI: https://doi.org/10.1002/cber.19861190810.

    Article  CAS  Google Scholar 

  40. M. Baudler, R. Becher, J. Germeshausen, Z. Anorg. Allg. Chem., 1987, 554, 7; DOI: https://doi.org/10.1002/zaac.19875541102.

    Article  CAS  Google Scholar 

  41. R. S. P. Turbervill, J. M. Goicoechea, Chem. Commun., 2012, 48, 1470; DOI: https://doi.org/10.1039/C1CC12089A.

    Article  CAS  Google Scholar 

  42. R. S. P. Turbervill, J. M. Goicoechea, Organometallics, 2012, 31, 2452; DOI: https://doi.org/10.1021/om300072z.

    Article  CAS  Google Scholar 

  43. R. S. P. Turbervill, J. M. Goicoechea, Eur. J. Inorg. Chem., 2014, 1660; DOI: https://doi.org/10.1002/ejic.201301011.

  44. M. Cicač-Hudi, J. Bender, S. H. Schlindwein, M. Bispinghoff, M. Nieger, H. Grützmacher, D. Gudat, Eur. J. Inorg. Chem., 2016, 649; DOI: https://doi.org/10.1002/ejic.201501017.

  45. V. Miluykov, A. Kataev, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Organometallics, 2005, 24, 2233; DOI: https://doi.org/10.1021/om050078u.

    Article  CAS  Google Scholar 

  46. V. A. Miluykov, A. V. Kataev, E. Hey-Hawkins, O. G. Sinyashin, Russ. Chem. Bull., 2007, 56, 304; DOI: https://doi.org/10.1007/s11172-007-0049-5.

    Article  CAS  Google Scholar 

  47. I. Bezkishko, V. Miluykov, A. Kataev, D. Krivolapov, I. Litvinov, O. Sinyashin, E. Hey-Hawkins, J. Organomet. Chem., 2008, 693, 3318; DOI: https://doi.org/10.1016/j.jorganchem.2008.08.006.

    Article  CAS  Google Scholar 

  48. V. A. Miluykov, L. R. Shakirova, I. A. Bezkishko, D. B. Krivolapov, O. G. Sinyashin, Russ. Chem. Bull., 2012, 61, 1483; DOI: https://doi.org/10.1007/s11172-012-0192-5.

    Article  CAS  Google Scholar 

  49. I. Bezkishko, V. Miluykov, O. Sinyashin, E. Hey-Hawkins, Phosphorus, Sulfur, Silicon, Rel. Elem., 2011, 186, 657; DOI: https://doi.org/10.1080/10426507.2010.508061.

    Article  CAS  Google Scholar 

  50. L. Kochetkova, I. Bezkishko, V. Miluykov, O. Sinyashin, Phosphorus, Sulfur, Silicon, Rel. Elem., 2015, 190, 863; DOI: https://doi.org/10.1080/10426507.2014.989434.

    Article  CAS  Google Scholar 

  51. L. R. Kochetkova, I. A. Bezkishko, V. A. Miluykov, D. R. Islamov, D. B. Krivolapov, O. N. Kataeva, O. G. Sinyashin, Russ. Chem. Bull., 2015, 64, 1912; DOI: https://doi.org/10.1007/s11172-015-1093-1.

    Article  CAS  Google Scholar 

  52. I. A. Bezkishko, A. A. Zagidullin, V. A. Miluykov, Russ. Chem. Bull., 2020, 69, 435; DOI: https://doi.org/10.1007/s11172-020-2782-y.

    Article  CAS  Google Scholar 

  53. R. Turbervill, J. Goicoechea, Chem. Commun., 2012, 48, 6100; DOI: https://doi.org/10.1039/C2CC32244G.

    Article  CAS  Google Scholar 

  54. R. Turbervill, A. Jupp, P. McCullough, D. Ergocmen, J. Goicoechea, Organometallics, 2013, 32, 2234; DOI: https://doi.org/10.1021/om4001296.

    Article  CAS  Google Scholar 

  55. R. Turbervill, J. Goicoechea, Inorg. Chem., 2013, 52, 5527; DOI: https://doi.org/10.1021/ic400448x.

    Article  CAS  PubMed  Google Scholar 

  56. I. A. Bezkishko, A. A. Zagidullin, A. V. Petrov, V. A. Miluykov, T. I. Burganov, S. A. Katsyuba, O. G. Sinyashin, J. Organomet. Chem., 2017, 844, 1; DOI: https://doi.org/10.1016/j.jorganchem.2017.05.037.

    Article  CAS  Google Scholar 

  57. A. V. Petrov, A. A. Zagidullin, T. I. Burganov, N. I. Shatalova, S. A. Katsyuba, V. A. Miluykov, Russ. Chem. Bull., 2019, 68, 445; DOI: https://doi.org/10.1007/s11172-019-2406-6.

    Article  CAS  Google Scholar 

  58. I. Bezkishko, A. Zagidullin, A. Petrov, V. Miluykov, O. Sinyashin, Phosphorus, Sulfur, Silicon, Rel. Elem., 2016, 191, 1425; DOI: https://doi.org/10.1080/10426507.2016.1211650.

    Article  CAS  Google Scholar 

  59. A. R. Jupp, J. M. Goicoechea, Angew. Chem., Int. Ed., 2013, 52, 10064; DOI: https://doi.org/10.1002/anie.201305235.

    Article  CAS  Google Scholar 

  60. D. Heift, Z. Benkö, H. Grützmacher, Angew. Chem., Int. Ed., 2014, 53, 6757; DOI: https://doi.org/10.1002/anie.201402884.

    Article  CAS  Google Scholar 

  61. X. Chen, S. Alidori, F. F. Puschmann, G. Santiso-Quinones, Z. Benkö, Z. Li, G. Becker, H. F. Grützmacher, H. Grützmacher, Angew. Chem., Int. Ed., 2014, 53, 1641; DOI: https://doi.org/10.1002/anie.201308220.

    Article  CAS  Google Scholar 

  62. A. R. Jupp, J. M. Goicoechea, J. Am. Chem. Soc., 2013, 135, 19131; DOI: https://doi.org/10.1021/ja4115693.

    Article  CAS  PubMed  Google Scholar 

  63. A. M. Tondreau, Z. Benkö, J. R. Harmer, H. Grützmacher, Chem. Sci., 2014, 5, 1545; DOI: https://doi.org/10.1039/C3SC53140F.

    Article  CAS  Google Scholar 

  64. I. A. Bezkishko, A. A. Zagidullin, V. A. Miluykov, O. G. Sinyashin, Russ. Chem. Rev., 2014, 83, 555; DOI: https://doi.org/10.1070/RC2014v083n06ABEH004442.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    A. A. Zagidullin, A. V. Petrov, I. A. Bezkishko & V. A. Miluykov

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  1. A. A. Zagidullin
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  2. A. V. Petrov
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  3. I. A. Bezkishko
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  4. V. A. Miluykov
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Correspondence to A. A. Zagidullin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1260–1268, July, 2021.

Based on the materials of the II Scientific Conference “Dynamic Processes in the Chemistry of Organoelement Compounds” (November 11–13, 2020, Kazan, Russia).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Zagidullin, A.A., Petrov, A.V., Bezkishko, I.A. et al. Alkali metal polyphosphides as intermediates in the synthesis of organophosphorus compounds from elemental phosphorus. Russ Chem Bull 70, 1260–1268 (2021). https://doi.org/10.1007/s11172-021-3209-0

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