A new method preparation of trimethylsilyl ethers of III-valence phosphorus

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Abstract

By the interaction of hydrophosphoryl compounds of various structures with hexamethyldisilazane at 20°C and in the presence of ZnSO4 and diethylamine, trimethylsilyl esters of acids of III-valent phosphorus were synthesized in high yields (89-94%). The reaction is completed in 4 hours, does not require the use of specially prepared solvents and an inert atmosphere, and can be proposed as a new synthetically useful and easy-to-perform method for the synthesis of trimethylsilyl esters of acids of III-valent phosphorus.

About the authors

V. P. Morgalyuk

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: morgaliuk@mail.ru

T. S. Strelkova

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

R. U. Takazova

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

A. G. Buyanovskaya

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

V. K. Brel

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

References

  1. Engel R., Cohen J.I. Synthesis of Carbon-Phosphorus Bonds. Boka Raton, London, New York, Washington: CRC Press. 2004, 47.
  2. Romanenko V.D., Shevchuk M.V., Kukhar V.P. Curr. Org. Chem. 2011, 15, 2774-2801. doi: 10.2174/138527211796378505
  3. Рагулин В.В. ЖОХ. 2012, 82, 1973-1982.
  4. Ragulin V.V. Russ. J. Gen. Chem. 2012, 82, 1928-1937. doi: 10.1134/S1070363212120055
  5. Yamamoto K., Hanjashi A., Suzuki S., Tsuji J. Organometallics. 1987, 6, 974-979. doi: 10.1021/om00148a014
  6. Debrouwer W., Hertren D., Heugebauert T.S.A., Boydas E.B., van Speybroeck V., Catak S., Stevens C.V. J. Org. Chem. 2017, 82, 188-201. doi: 10.1021/acs.joc.6b02340
  7. Guin J., Souram W., van Gemmeren M., List B. Angew. Chem. Int. Ed. 2015, 54, 355-358. doi: 10.1002/anie.201409411
  8. Issleib K., Walther B. Angew. Chem. Int. Ed. 1967, 6, 88. doi: 10.1002/anie.196700881
  9. Liotta D., Sunay V., Ginsberg S. J. Org. Chem. 1982, 47, 2227-2229. doi: 10.1021/jo00132a062
  10. Li Zh., Zhu Ch., Zhao Y., Phosp. Sulf. Relat. Elem. 1994, 86, 229-232. doi: 10.1080/10426509408018408
  11. Чернышев Е.А., Бугеренко Е.Ф., Акатьева А.С., Наумов А.Д. ЖОХ. 1975, 45, 242-243.
  12. Chernyshev E.A., Bugerenko E.F., Akat'eva A.S., Naumov A.D. J. Gen. Chem. USSR. 1975, 45, 231.
  13. Sekine M., Futatsugi T., Yamada K., Hata Ts. J. Chem. Soc., Perkin Trans. 1. 1982, 11, 2509-2513. doi: 10.1039/P19820002509
  14. Sekine M., Futatsugi T., Yamada K., Hata Ts. Bull. Soc. Chem. Jpn. 1982, 55, 224-238. doi: 10.1246/bcsj.55.224
  15. Бондаренко Н.А., Цветков Е.Н. ЖОХ. 1991. 59, 1361-1364.
  16. Bondarenko N.A., Tsvetkov E.N. J. Gen. Chem. USSR. 1989, 59, 1361-1364.
  17. Hammerschmidt F. Liebigs Ann. Chem. 1991, 469-475. doi: 10.1002/jlac.199119910185
  18. McGrath J.W., Hammerschmidt F., Prensser W., Quinn J.P., Schweifer A. J. Org. Biomol. Chem. 2009, 7, 1944-1953. doi: 10.1039/b821829c
  19. Моргалюк В.П., Стрелкова Т.В., Буяновская, А.Г. Брель В.К. ЖОрХ. 2019, 55, 1469-1471.
  20. Morgalyuk V.P., Strelkova T.V., Buyanovskaya A.G., Brel V.K. Russ. J. Org. Chem. 2019, 55, 1442-1443. doi: 10.1134/S1070428019090276
  21. Morgalyuk V., Strelkova T., Brel V. Monatsh. Chem. 2019, 150, 1993-1997. doi: 10.1007/s00706-019-02511-6
  22. Morgalyuk V.P., Strelkova T.V., Nifant'ev E.E., Brel V.K. Phosp. Sulf. Relat. Elem. 2016, 191, 1462-1463. doi: 10.1080/10426507.2016.1212040
  23. Гомеля Н.Д., Фещенко Н.Г. ЖОХ. 1991, 61, 2541-2544.
  24. Gomelya N.D., Feschenko N.G. J. Gen. Chem. USSR. 1991, 61, 2338-2341.
  25. Santschi N., Togni A. J. Org. Chem. 2011, 76, 4189-4193. doi: 10.1021/jo200522w
  26. Nishizawa M., Shioji K., Kurauchi Y., Okuma K., Kohno M. Bull. Soc. Chem. Jpn. 2007, 80, 495-497. doi: 10.1246/bcsj.80.495
  27. Гареев Р.Д., Логинова Г.М., Пудовик А.Н. ЖОХ. 1978, 48, 1688-1698.
  28. Gareev R.D., Loginova G.M., Pudovik A.N. J. Gen. Chem. USSR. 1978, 48, 1544-1552.
  29. Morita I., Chokai Sh., Tsuda M., Kise M., Sugiyama M. Chem. Pharm. Bull. 1988, 36, 1135-1138. doi: 10.1248/cpb.36.1135
  30. Morgalyuk V.P., Strelkova T.V., Nifant'ev E.E., Brel V.K. Mendeleev Comm. 2016, 26, 397-398. doi: 10.1016/j.mencom.2016.09.010

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