Skip to main content
Log in

Reactions of monothio, monoseleno, and selenothio acids of phosphorus with aliphatic diazo compounds

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

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.

Literature cited

  1. A. Heiter, Jahresber, 328 (1863); 302 (1865).

  2. A. Baeyer and S. Oekonomides, Chem. Ber.,15, 2093 (1882);16, 2193 (1883).

    Google Scholar 

  3. A. Brändström, Arkiv, Kemi,7, 81 (1954); 11, 567 (1957).

    Google Scholar 

  4. A. N. Nesmeyanov and M. I. Kabachnik, Zh. Obshch. Khim.,25, 41 (1955).

    Google Scholar 

  5. N. Kornblum, P. J. Berrigan, W. J. le Noble, J. Am. Chem. Soc.,85, 1141 (1963); N. Kornblum, R. Seltzer, and P. Haberfield, ibid.,85, 1148 (1963); N. Kornblum and P. Pink, Tetrahedron,19, 17 (1963).

    Google Scholar 

  6. W. J. le Noble and H. F. Morris, J. Org. Chem.,34, 1969 (1969).

    Google Scholar 

  7. A. G. Pinkus, A. B. Wu, and J. G. Lindberg, Chem. Commun., 859 (1970); A. L. Kurts, A. Masias, I. P. Beletskaya, and O. A. Reutov, Tetrahedron,27, 4759 (1971); A. L. Kurts, P. I. Dem'yanov, A. Masias, I. P. Beletskaya, and O. A. Reutov, ibid.,24, 4769 (1971); A. L. Kurts, N. K. Genkina, A. Masias, I. P. Beletskaya, and O. A. Reutov, ibid.,24, 4777 (1971); A. L. Kurts, P. I. Dem'yanov, I. P. Beletskaya, and O. A. Reutov, Zh. Org. Khim.,9, 1313 (1973); A. L. Kurts, I. P. Beletskaya, and O. A. Reutov, Vestn. Mosk. Univ., Ser. Khimiya, No. 4, 387 (1974); H. O. House, R. A. Auerbach, M. Gall, and N. D. Peet, J. Org. Chem.,38, 514 (1973); L. M. Jackman and R. C. Haddon, J. Am. Chem. Soc.,95, 3687 (1973); E. A. Noe and M. Raban, ibid.,96, 6184 (1974); O. A. Reutov and A. L. Kurts, Usp. Khim.,46, 1964 (1977).

  8. R. Gompper and H.-U. Wagner, Angew. Chem.,88, 389 (1976).

    Google Scholar 

  9. G. Klopman and R. F. Hudson, Theor. Chim. Acta,8, 165 (1967); G. Klopman, J. Am. Chem. Soc.,90, 223 (1968); R. F. Hudson, Angew. Chem.,85, 63 (1973); ibid., Int. Ed.,12, 36 (1973).

    Google Scholar 

  10. R. G. Pearson, Hard and Soft Acids and Bases, Hutchinson and Ross, Dowden, Stroudsburg, Pa. (1973).

    Google Scholar 

  11. T. A. Mastryukova, Phosphorus Sulfur,1, 211 (1976).

    Google Scholar 

  12. C. J. Pedersen and H. K. Frensdorff, Angew. Chem. Int. Ed.,11, 16 (1972).

    Google Scholar 

  13. R. A. More O'Ferrall, Adv. Phys. Org. Chem.,5 331 (1967); R. A. More O'Ferrall, W. K. Kwok, and S. I. Miller, J. Am. Chem. Soc.,86, 5553 (1964).

    Google Scholar 

  14. J. D. Roberts, W. Watanabe, and E. McMahon, J. Am. Chem. Soc.,73, 2521 (1951); J. D. Roberts and C. M. Regan, ibid.,74, 3695 (1952); J. D. Roberts, C. M. Regan, and I. Allen, ibid.,74, 3679 (1952); J. D. Roberts, C. M. Regan, ibid.,76, 939 (1954); J. D. Roberts, C. M. Regan, ibid.,75, 2167, 4102 (1953).

    Google Scholar 

  15. K. Bowden, A. Buckley, and N. B. Chapman, J. Chem. Soc., 3880 (1964); A. Buckley, N. B. Chapman, M. R. J. Dack, J. Shorter, and H. M. Wall, ibid., Sec. B, 631 (1968); N. B. Chapman, M. R. J. Dack, and J. Shorter, ibid., Sec. B. 834 (1971); N. B. Chapman, M. R. J. Dack, D. I. Newman, J. Shorter, and R. Wilkinson, J. Chem. Soc., Perkin Trans. II, 962 (1974); N. B. Chapman, M. R. J. Dack, D. I. Newman, J. Shorter, and R. Wilkinson, ibid., 971 (1974).

  16. D. Bethell and J. D. Callister, J. Chem. Soc.,3801, 3808 (1963).

    Google Scholar 

  17. J. F. Lane and R. L. Feller, J. Am. Chem. Soc.,73, 4230 (1951).

    Google Scholar 

  18. R. Huisgen and C. Rüchardt, Liebigs, Ann. Chem.,601, 1 (1956).

    Google Scholar 

  19. J. F. McGarrity and T. Smyth, Chem. Commun., 347 (1977).

  20. F. Arndt, B. Eistert, R. Gompper, and W. Walter, Ber.,94, 2125 (1961).

    Google Scholar 

  21. F. A. Long and M. A. Paul, Chem. Revs.,57, 935 (1957); K. D. Warren, J. Chem. Soc., 2561 (1961).

    Google Scholar 

  22. C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell Univ. Press, Ithaca (1953).

    Google Scholar 

  23. H. Dahn and H. Gold, Helv. Chim. Acta,46, 983 (1963).

    Google Scholar 

  24. R. Gompper, Angew. Chem.,76, 412 (1964).

    Google Scholar 

  25. T. A. Mastryukova, M. Orlov, L. S. Butorina, E. I. Matrosov, T. M. Shcherbina, and M. I. Kabachnik, Zh. Obshch. Khim.,44, 1001 (1974).

    Google Scholar 

  26. O. Exner, Collect. Czech. Chem. Commun.,26, 1 (1961).

    Google Scholar 

  27. M. Orlov, T. B. Sakharova, L. S. Butorina, E. I. Matrosov, and T. A. Mastryukova, in: Chemistry and Application of Organophosphorus Compounds, Proceedings of the Fifth Conference, 1972 [in Russian], Nauka (1974), p. 358.

  28. T. A. Mastryukova, M. Orlov, D. Eremich, and M. I. Kabachnik, Zh. Obshch. Khim.,44, 2403 (1974).

    Google Scholar 

  29. T. A. Mastryukova, L. S. Butorina, and M. I. Kabachnik, Zh. Obshch. Khim.,43, 2083 (1973).

    Google Scholar 

  30. T. A. Mastryukova, L. S. Butorina, E. I. Matrosov, and M. I. Kabachnik, Zh. Obshch. Khim.,47, 748 (1977).

    Google Scholar 

  31. T. A. Mastryukova, L. S. Butorina, V. N. Kushnir, and M. I. Kabachnik, Zh. Obshch. Khim.,47, 981 (1977).

    Google Scholar 

  32. T. A. Mastryukova, R. M. Kalyanova, G. K. Genkina, T. M. Shcherbina, V. A. Svoren', and M. I. Kabachnik, Zh. Obshch. Khim.,47, 2723 (1977).

    Google Scholar 

  33. T. A. Mastryukova, L. S. Butorina, A. B. Uryupin, V. A. Svoren', and M. I. Kabachnik, Zh. Obshch. Khim.,48, 257 (1978).

    Google Scholar 

  34. T. A. Mastryukova, Ya. Mikhal'skii, A. B. Uryupin, Z. Skshiptshin'skii, and M. I. Kaba-Kabachnik, Zh. Obshch. Khim.,48, 463 (1978).

    Google Scholar 

  35. T. A. Mastryukova, Ya. Mikhal'skii, A. B. Uryupin, Z. Skshiptshin'skii, and M. I. Kabachnik, Zh. Obshch. Khim.,48, 1447 (1978).

    Google Scholar 

  36. T. A. Mastryukova, A. B. Uryupin, and M. I. Kabachnik, Zh. Obshch. Khim.,48, No. 10 (1978).

  37. N. Kornblum, R. A. Smiley, R. K. Blackwood, and D. C. Iffland, J. Am. Chem. Soc.,77, 6269 (1955), N. Kornblum et al, ibid.,76, 3209 (1954); N. Kornblum et al., ibid.,77, 5528 (1955).

    Google Scholar 

  38. C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell Univ. Press, Ithaca (1969).

    Google Scholar 

  39. M. I. Kabachnik, T. A. Mastryukova, A. E. Shipov, and T. A. Melentyeva, Tetrahedron,9, 10 (1960).

    Google Scholar 

  40. A. Markowska, Bull. Acad. Pol. Sci. Ser. Sci. Chim.,13, 149 (1965).

    Google Scholar 

  41. T. A. Mastryukova and M. I. Kabachnik, Usp. Khim.,38, 1751 (1969).

    Google Scholar 

  42. E. S. Amis, Solvent Effects on Reaction Rates, Academic Press, New York (1964).

    Google Scholar 

  43. M. T. Shafik, D. Bradway, F. Y. Biros, and H. F. Enos, J. Agr. Food Chem.,18, 1174 (1970).

    Google Scholar 

  44. J. D. Dickinson and C. Eaborn, J. Chem. Soc., 3574 (1959).

  45. K. D. Warren, J. Chem. Soc., 2561 (1961).

  46. W. Jugelt and L. Berseck, Tetrahedron,26, 5557 (1970).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2040–2061, September, 1978.

This paper was printed according to a decision of the editorial board of the journal on March 2, 1978.

The following participated in this series of studies: L. S. Lutorina', G. K. Genkina, D. Eremich, R. M. Kalyanova, E. I. Matresov, Ya. Mikhal'skii, M. Orlov, V. A. Svoren', Z. Skshiptship'skii, A. B. Uryupin, and T. M. Shcherbina. We take this opportunity to thank them again.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mastryukova, T.A., Kabachnik, M.I. Reactions of monothio, monoseleno, and selenothio acids of phosphorus with aliphatic diazo compounds. Russ Chem Bull 27, 1795–1814 (1978). https://doi.org/10.1007/BF00929227

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00929227

Keywords

Navigation