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A new approach towards synthesis of phosphorylated alkenes

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Abstract

New method of synthesis of trans-vinylphosphonates via reaction of trimethylsilyl(methyl)phosphonites with carbonyl compounds in the presence of carbon tetrachloride has been developed. The reaction involves formation of C-trimethylsilyl substituted ylides and 2-chloro-1,2λ5-oxaphosphetanes as intermediates.

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References

  1. Giordano, C. and Castaldi, G., J. Org. Chem., 1989, vol. 54, no. 6, p. 1470. DOI: 10.1021/jo00267a050.

    Article  CAS  Google Scholar 

  2. Maryanoff, B.E. and Reitz, A.B., Chem. Rev., 1989, vol. 89, no. 4, p. 863. DOI: 10.1021/cr00094a007.

    Article  CAS  Google Scholar 

  3. Minami, T. and Motoyoshiya, J., Synthesis, 1992, no. 4, p. 333. DOI: 10.1055/s-1992-26103.

    Google Scholar 

  4. Stowasser, B., Budt, K.-H., Jian-Qi, L., Peyman, A., and Ruppert, D., Tetrahedron Lett., 1992, vol. 33, no. 44, p. 6625. DOI: 10.1016/S0040-4039(00)61002-X.

    Article  CAS  Google Scholar 

  5. Hirschmann, R., Smith, A.B., Taylor, C.M., Benkovic, P.A., Taylor, S.D., Yager, K.M., Sprengeler, P.A., and Benkovic, S.J., Science, 1994, vol. 265, no. 5169, p. 234. DOI: 10.1126/science.8023141.

    Article  CAS  Google Scholar 

  6. Graeve, R., Thorwart, W., Raiss, R., Weithmann, K.U., and Mullner, S., US Patent 5627173, 1997.

  7. Lennon, P.J., US Patent 5434288, 1995.

  8. Holstein, S.A., Cermak, D.M., Wiemer, D.F., Lewis, K., and Hohl, R., J. Bioorg. Med. Chem., 1998, vol. 6, no. 6, p. 687. DOI: 10.1016/S0968-0896(98)00034-0.

    Article  CAS  Google Scholar 

  9. Lazrek, H.B., Witvrouw, M., Pannecouque, C., and De Clerq, E., Tetrahedron, 1998, vol. 54, no. 15, p. 3807. DOI: 10.1016/S0040-4020(98)00107-0.

    Article  CAS  Google Scholar 

  10. Harnden, M.R., Parkin, A., Parratt, M.J., and Perkins, R.M., J. Med. Chem., 1993, vol. 36, no. 10, p. 1343. DOI: 10.1021/jm00062a006.

    Article  CAS  Google Scholar 

  11. Raboisson, P., Baurand, A., Cazenave, J.-P., Gachet, C., Schutz, D., Spiess, B., and Bourguigon, J.-J., J. Org. Chem., 2002, vol. 67, no. 23, p. 8063. DOI: 10.1021/jo026268l.

    Article  CAS  Google Scholar 

  12. Enders, D., Wahl, H., and Papadopoulos, K., Tetrahedron, 1997, vol. 53, no. 23, p. 12961. DOI: 10.1016/S0040-4020(97)00814-4.

    Article  CAS  Google Scholar 

  13. Robiette, R., Defacqz, N., Stofferis, J., and Marchand-Brynaert, J., Tetrahedron, 2003, vol. 59, no. 23, p. 4167. DOI: 10.1016/S0040-4020(03)00580-5.

    Article  CAS  Google Scholar 

  14. Arimori, S., Kouno, R., Okauchi, T., and Minami, T., J. Org. Chem., 2002, vol. 67, no. 21, p. 7303. DOI: 10.1021/jo020403c.

    Article  CAS  Google Scholar 

  15. Yokomatsu, T., Yamagishi, T., Suemune, K., Yoshida, Y., and Shibuya, S., Tetrahedron, 1998, vol. 54, no. 5, p. 767. DOI: 10.1016/S0040-4020(97)10341-6.

    Article  CAS  Google Scholar 

  16. Kim, D.Y., and Rhie, D.Y., Tetrahedron, 1997, vol. 53, no. 40, p. 13603. DOI: 10.1016/S0040-4020(97)00880-6.

    Article  CAS  Google Scholar 

  17. Junker, H.-D. and Fessner, W.-D., Tetrahedron Lett., 1998, vol. 39, no. 3, p. 269. DOI: 10.1016/S0040-4039(97)10498-1.

    Article  CAS  Google Scholar 

  18. Jin, S. and Gonsalves, K.E., Macromolecules, 1998, vol. 31, no. 4, p. 1010. DOI: 10.1021/ma9707289.

    Article  CAS  Google Scholar 

  19. UK Patent 2102427, 1983; C. A., 1983, vol. 99, p. 88368d.

  20. Jin, J.I., US Patent 4031054, 1977; C. A., 1977, vol. 87, p. 54500.

  21. Joseph, P. and Tretsiakova-McNally, S., ACS Symposium Series, 2012, vol. 1118, ch. 13, p. 37. DOI: 10.1021/bk-2012-1118.ch003.

    Article  CAS  Google Scholar 

  22. Howell, B.A. and Dumitrascu, A., ACS Symposium Series, 2012, vol. 1118, ch. 17, p. 235. DOI: 10.1021/bk-2012-1118.ch017.

    Article  CAS  Google Scholar 

  23. Kolodiazhnyi O.I., Russ. Chem. Rev., 1991, vol. 60, no. 4, p. 391.

    Article  Google Scholar 

  24. Kolodiazhnyi, O.I. Phosphorus Ylides. Chemistry and Application in Organic Synthesis. Weinheim; New York; Chichester: J. Wiley-VCH, 1999. 565 p.

    Google Scholar 

  25. Kolodiazhnyi, O.I., Tetrahedron Lett., 1985, vol. 26, no. 4, p. 439. DOI: 10.1016/S0040-4039(00)61905-6.

    Article  Google Scholar 

  26. Kolodiazhnyi, O.I., Tetrahedron Lett., 1981, vol. 22, no. 13, p. 1231. DOI: 10.1016/S0040-4039(01)90282-5.

    Article  CAS  Google Scholar 

  27. Kolodiazhnyi, O.I., Zh. Obshch. Khim., 1986, vol. 56, no. 2, p. 253.

    Google Scholar 

  28. Zhong, P., Xiong, Z.X., and Huani, X., Synth. Commun., 2000, vol. 30, no. 2, p. 273. DOI: 10.1080/00397910008087318.

    Article  CAS  Google Scholar 

  29. Xu, Y., Flavin, M.T., and Xu, Z.-Q., J. Org. Chem., 1996, vol. 61, no. 21, p. 7697. DOI: 10.1021/jo9608275.

    Article  CAS  Google Scholar 

  30. Blaszczyk, R., and Gajda, T., Heteroatom Chem., 2007, vol. 18, no. 7, p.732. DOI: 10.1002/hc.20371.

    Article  CAS  Google Scholar 

  31. Brunner, H., Le Cousturier de Courcy, N., and Genêt, J.-P., Synlett, 2000, no. 2, p. 201. DOI: 10.1055/s-2000-6482.

    Google Scholar 

  32. Kolodiazhnyi, O.I., and Golokhov, D.V., Zh. Obshch. Khim., 1987, vol. 57, no. 11, p. 2640.

    Google Scholar 

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 1, Kiev, 02094, Ukraine

    O. I. Kolodyazhnii & A. O. Kolodyazhnaya

Authors
  1. O. I. Kolodyazhnii
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  2. A. O. Kolodyazhnaya
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Correspondence to O. I. Kolodyazhnii.

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Original Russian Text © O.I. Kolodyazhnii, A.O. Kolodyazhnaya, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 2, pp. 185–191.

To the 80th Anniversary of B.I. Ionin

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Kolodyazhnii, O.I., Kolodyazhnaya, A.O. A new approach towards synthesis of phosphorylated alkenes. Russ J Gen Chem 85, 359–365 (2015). https://doi.org/10.1134/S1070363215020024

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  • DOI: https://doi.org/10.1134/S1070363215020024

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