Skip to main content
Log in

Heteroorganic betaines

1. Synthesis of betaines containing the+P−C−Si−S and+P−C−C−S fragments and their characterization by multinuclear NMR spectroscopy

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A method for the synthesis of a new class of betaines,viz., R3 1P+CR2R3SiR4R5S, was developed. The experimental evidence for the intermediate formation of betaines R3 1P+−CR2R3−CR4R5−S in the Wittig reaction for a series of thiocarbonyl compounds was obtained. A comparative analysis of the NMR spectra of betaines containing the+P−C−Si−S and+P−C−C−S fragments was performed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. B. E. Maryanoff and A. B. Reitz,Chem. Rev., 1989,89, 863; (b) A. W. Jonson,Ylides and Imines of Phosphorus, Wiley-Interscience, New York, 1993; (c) O. I. Kolodiazhnyi,Phosphorus Ylides. Chemistry and Application in Organic Synthesis, Wiley-VCH, Weinheim-New York-Chichester, 1999; (d) O. I. Kolodyazhnyi,Khimiya ilidov fosfora [Chemistry of Phosporus Ylides], Naukova Dumka, Kiev, 1994 (in Russian); (e) A.-H. Li, L.-X. Dai, and V. K. Aggrarval.Chem. Rev., 1997,97, 2341.

    Article  CAS  Google Scholar 

  2. G. Wittig and U. Schöllkopf.Chem. Ber., 1954,87, 1318; (b) G. Wittig and W. Haag,Chem. Ber., 1955,88, 1654.

    Google Scholar 

  3. E. Vedejs and M. J. Peterson, inAdvances in Carbanion Chemistry, Ed. V. Snieckus, JAI Press, Greenwich (CT), 1996,2, 1; (b) E. Vedejs and M. J. Peterson,Top. Stereochem., 1994,21, 1; (c) E. Vedejs and C. F. Marth, inPhosphorus-31 NMR Spectral Properties in Compound Characterization and Structural Analysis. Eds. L. D. Quin and J. G. Verkade, VCH, New York, 1994, 297.

    Google Scholar 

  4. T. Kawashima and R. Okazaki,Synlett, 1996, 600; (b) T. Kawashima, T. Soda, and R. Okazaki,Angew. Chem., Int. Ed. Engl., 1996,35, 1096; (c) F. Ohno, T. Kawashima, and R. Okazaki,J. Am. Chem. Soc., 1996,118, 697; (d) T. Kawashima, F. Ohno, R. Okazaki, H. Ikeda, and S. Inagaki,J. Am. Chem. Soc., 1996,118, 12455; (e) T. Kawashima and R. Okazaki,Angew. Chem., Int. Ed. Engl., 1997,36, 2500; (f) F. Ohno, T. Kawashima, and R. Okazaki,Chem. Commun., 1997, 1671.

  5. R. Höller and H. Lischka,J. Am. Chem. Soc., 1980,102, 4632; (b) F. Volatron and O. Eisenstein,J. Am. Chem. Soc., 1987,109, 1; (c) F. Mari, P. M. Lahti, and W. E. McEwen,J. Am. Chem. Soc., 1992,114, 813; (d) T. Naito, S. Nagase, and H. Yamataka,J. Am. Chem. Soc., 1994,116, 10080; (e) H. Yamataka and S. Nagase,J. Am. Chem. Soc., 1998,.120, 7530.

    Article  Google Scholar 

  6. C. Geletneky, F.-H. Försterling, W. Bock, and S. Berger,Chem. Ber., 1993,126, 2397; (b) R. A. Neumann and S. Berger,Eur. J. Org. Chem., 1998, 1085.

    CAS  Google Scholar 

  7. I. V. Borisova, N. N. Zemlyansky, V. K. Belsky, N. D. Kolosova, A. N. Sobolev, Yu. N. Luzikov, Yu. A. Ustynyuk, and I. P. Beletskaya,J. Chem. Soc., Chem. Commun., 1982, 1090; (b) I. V. Borisova, N. N. Zemlyanskii, Yu. N. Luzikov, Yu. A. Ustynyuk, V. K. Bel'skii, N. D. Kolosova, M. M. Shtern, and I. P. Beletskaya,Dokl. Akad. Nauk SSSR, 1983.269, 369 [Dokl. Chem., 1983,269, 90 (Engl. Transl.)]. (c) I. V. Borisova, N. N. Zemlyanskii, Yu. A. Ustynyuk, I. P. Beletskaya, and E. A. Chernyshev,Metalloorg. Khim., 1992,5, 548 [Organomet. Chem. USSR, 1992,5, 262 (Engl. Transl.)].

  8. A. G. Brook and A. MacMillan,J. Organomet. Chem., 1988,341, C9.

    Article  Google Scholar 

  9. K. Okuma,Rev. Heteroat. Chem., 1992,7, 117; (b) G. M. Li, M. Segi, T. Kamogawa, and T. Nakajima,Chem. Express, 1993,8, 53; (c) K. Okuma, T. Ishida, S. Morita, H. Ohta, and T. Inoue,Heteroat. Chem., 1995,6, 265; (d) S. Wilker, C. Laurent, C. Sarter, C. Puke, and G. Erker,J. Am. Chem. Soc., 1995,117, 7293.

    CAS  Google Scholar 

  10. I. V. Borisova, N. N. Zemlyanskii, A. K. Shestakova, and Yu. A. Ustynyuk,Izv. Akad. Nauk, Ser. Khim., 1993,2140 [Russ. Chem. Bull., 1993,42, 2053 (Engl. Transl.)]; (b) I. V. Borisova, N. N. Zemlyanskii, A. K. Shestakova, and Yu. A. Ustynyuk,Izv. Akad. Nauk. Ser. Khim., 1993, 2143 [Russ. Chem. Bull., 1993,42, 2056 (Engl. Transl.)]; (c) I. V. Borisova, N. N. Zemlyanskii, Yu. A. Ustynyuk, V. N. Khrustalev, S. V. Lindernan, and Yu. T. Struchkov,Izv. Akad. Nauk, Ser. Khim., 1994, 339 [Russ. Chem. Bull., 1994,43, 318 (Engl. Transl.)]; (d) I. V. Borisova, N. N. Zemlyansky, A. K. Shestakova, and Yu. A. Ustynyuk,Mendeleev Commun., 1996, 90; (e) I. V. Borisova, N. N. Zemlyansky, A. K. Shestakova, V. N. Khrustalev, Yu. A. Ustynyuk, and E. A. Chernyshev,18th Int. Conf. on Organomet. Chem. (August 1998), Abstrs., Part 1, Munich (Germany), 1998, B18.

  11. A. G. Brook and A. M. Brook,Adv. Organomet. Chem., 1996,39, 71; (b) I. Hemme and U. Klingebiel,Adv. Organomet. Chem., 1996,39, 159; (c) M. Driess,Adv. Organomet. Chem., 1996,39, 193; (d) R. Okazaki and R. West,Adv. Organomet. Chem., 1996,39, 232: (e) N. Auner,J. Prakt. Chem. Chem. Ztg., 1995,337, 79: (f) V. N. Khabashesku, K. N. Kudin, J. Tamas, S. E. Boganov, J. L. Margrave, and O. M. Nefedov,J. Am. Chem. Soc., 1998,120, 5005.

    Article  CAS  Google Scholar 

  12. T. A. Albright, W. J. Freeman, and E. E. Schweizer,J. Am. Chem. Soc., 1975,97, 2542; (b) T. A. Albright, M. Gordon, W. J. Freeman, and E. E. Schweizer,J. Am. Chem. Soc., 1976,98, 6249; (c) K. A. O. Starzewski and H. T. Dieck,Phosphorus, 1976,6, 177;(d) H.-G. Horn and M. Hemeke,Chem. Zig., 1982,106, 263; (e) R. Köster, D. Simie, and M. A. Grassberger,Ann., 1970,739, 211; (f) J. B. Hendrickson, M. L. Maddox, J. J. Sims, and H. D. Kaesz,Tetrahedron, 1964,20, 449; (g) E. V. van den Berghe and G. P. van der Kelen,J. Organomet. Chem., 1976,122, 329.

    Article  Google Scholar 

  13. K.-H. Dreihäupt, K. Angermaier, J. Riede, and H. Schmidbaur,Chem. Ber., 1994,127, 1599; (b) H. Schmidbaur, R. Pichl, and G. Muller,Chem. Ber., 1987,120, 789; (c) H. Schmidbaur and W. Tronich,Chem. Ber., 1968,101, 595.

    Google Scholar 

  14. I. V. Borisova, N. N. Zemlyanskii, A. K. Shestakova, V. N. Khrustalev, Yu. A. Ustynyuk, and E. A. Chernyshev,Izv. Akad. Nauk, Ser. Khim., 2000, No. 8 [Russ. Chem. Bull., 2000,49, No. 8 (Engl. Transl.)].

  15. Z. Yoshida, T. Kawase, and S. Yoneda,Tetrahedron, Lett., 1975, 235; (b) E. Vedejs, D. A. Perry, and R. G. Wilde,J. Am. Chem. Soc., 1996,108, 2985.

    Google Scholar 

  16. C. Puke, G. Erker, N. C. Aust, E.-U. Würtheim, and R. Fröhlich,J. Am. Chem. Soc., 1998,120, 4863.

    Article  CAS  Google Scholar 

  17. D. S. Pederson, S. scheibge, N. H. Nilsson, and S.-O. Lawesson,Bull. Soc. Chim. Belg., 1978,87, 223.

    Article  Google Scholar 

  18. M. Weidenbruch, W. Schiffer, G. Hagele, and W. Peters,J. Organomet. Chem., 1975,90, 145.

    Article  CAS  Google Scholar 

  19. J. H. So and P. Boudjouk,Synthesis, 1989, 306.

  20. M. D. Mizhiritskii and V. O. Reiskhfel'd,Usp. Khim., 1988,47, 803 [Russ. Chem. Res., 1988,47, 447 (Engl. Transl.)].

    Google Scholar 

  21. U. H. M. Fagerlund and D. R. Idler,J. Am. Chem. Soc., 1957,79, 6473; (b) N. A. Milas and C. P. Priesing.J. Am. Chem. Soc., 1957,79, 6295; (c) R. Baumgartner, W. Sawodny, and J. Goubeau,Z. anorg. allgem. Chem., 1964,333, 171.

    CAS  Google Scholar 

  22. H. J. Bestmann, W. Stransky, O. Vostrovsky,Chem. Ber., 1976,109, 1694.

    CAS  Google Scholar 

  23. K. Issleib, M. Lischewski, and A. Zschunke,Org. Magn. Reson., 1973,5, 401.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 922–930, May, 2000.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Borisova, I.V., Zemlyanskii, N.N., Shestakova, A.K. et al. Heteroorganic betaines. Russ Chem Bull 49, 920–928 (2000). https://doi.org/10.1007/BF02494719

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02494719

Key words

Navigation