2,3-dimethoxyperhydro-1,4,2,3-dioxadiazine: Synthesis, conformation, and conversion to 1-(2-hydroxyethoxy)-2-methoxydiazene-1-oxide. Crystal structure of 1-[2-(para-nitrobenzoyloxy)-ethoxy]-2-methoxydiazene-1-oxide

  • V. F. Rudchenko
  • S. M. Ignatov
  • I. I. Chervin
  • A. É. Aliev
  • M. O. Dekaprilevich
  • Yu. T. Struchkov
  • R. G. Kostyanovskii
Organic Chemistry
  • 26 Downloads

Abstract

The oxidation of 1,2-bis(methoxyaminooxy)ethane (3) with PbO2 afforded 2,3-dimethoxyperhydro-1,4,2,3-dioxadiazine (4) in the form of the 55:45 mixture of thetrans-4ee- andcis-4 isomers. The barrier of the ring conversion (ΔG238=11.3 kcal/mole) of thecis-4 isomer was determined by the method of13C NMR. The regio- and stereospecific stereoelectronically controlled reaction of (4) withpara-nitrobenzoic acid gives the equimolar mixture of methylpara-nitrobenzoate and the 1,2-dialkoxydiazene oxide (5), the structure of which, and the (E)-configuration, were shown by the x-ray structural data of its acylation product — the diazene oxide (6).

Keywords

dialkoxyaminyl biradicals 2,3-dimethoxyperhydro-1,4,2,3-dioxadiazine dialkoxydiazene oxides conformation inversion x-ray structure analysis stereoelectronic control 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. I. Prokof'ev, V. F. Rudchenko, S. M. Ignatov, I. I. Chervin, and R. G. Kostyanovskii,Izv. Akad. Nauk, Ser. Khim., No. 8, 1819 (1989).Google Scholar
  2. 2.
    M. Yu. Antipin, Yu. T. Struchkov, V. F. Rudchenko, S. M. Ignatov, and R. G. Kostyanovskii,Izv. Akad. Nauk, Ser. Khim., No. 8, 1825 (1989).Google Scholar
  3. 3.
    Y. Miura and T. Ohana,J. Org. Chem.,53, No. 24, 5770 (1988); Y. Miura, T. Ohana, and T. Kunishi,Bull. Chem. Soc. Jpn.,63, No. 1, 269 (1990).Google Scholar
  4. 4.
    J. E. Baldwin,J. Chem. Soc. Chem. Commun., No. 18, 734 (1976).Google Scholar
  5. 5.
    V. F. Rudchenko, V. I. Shevchenko, and R. G. Kostyanovskii,Izv. Akad. Nauk, Ser. Khim., No. 3, 598 (1986); V. F. Rudchenko, S. M. Ignatov, I. I. Chervin, V. S. Nosova, and R. G. Kostyanovskii,Izv. Akad. Nauk, Ser. Khim., No. 5, 1158 (1986).Google Scholar
  6. 6.
    D. W. Dixon, R. H. Weiss, and W. M. Nelson,Tetrahedron Lett.,24, No. 41, 4393 (1983).Google Scholar
  7. 7.
    R. H. Weiss, E. Furfine, E. Hausleden, and D. W. Dixon,J. Org. Chem.,49, No. 25, 4969 (1984).Google Scholar
  8. 8.
    R. A. Kaba and K. U. Ingold,J. Am. Chem. Soc.,98, No. 23, 7375 (1976); K. Brink and R. Mattes,Chem. Ber.,118, No. 2, 564 (1985); V. G. Shtamburg, V. F. Rudchenko, Sh. S. Nasibov, I. I. Chervin, A. P. Pleshkova, and R. G. Kostyanovskii,Izv. Akad. Nauk, Ser. Khim., No. 10, 2327 (1981); V. F. Rudchenko, V. I. Shevchenko, and R. G. Kostyanovskii,Izv. Akad. Nauk, Ser. Khim., No. 3, 606 (1986).Google Scholar
  9. 9.
    S. Castellano and A. A. Bothner-By,J. Chem. Phys.,41, No. 12, 3864 (1964).Google Scholar
  10. 10.
    J. B. Lambert,Acc. Chem. Res.,4, No. 1, 87 (1971).Google Scholar
  11. 11.
    H. R. Buys,Rec. Trav. Chim.,88, No. 9, 1003 (1969).Google Scholar
  12. 12.
    A. B. Zolotoi, O. A. D'yachenko, I. I. Chervin, V. F. Rudchenko, L. O. Atovmyan, and R. G. Kostyanovskii,Khim. Geterotsikl. Soedin., No. 10, 1341 (1985).Google Scholar
  13. 13.
    S. F. Nelsen,Acc. Chem. Res.,11, No. 1, 14 (1978).Google Scholar
  14. 14.
    S. F. Nelsen and G. R. Weisman,J. Am. Chem. Soc.,98, No. 11, 3281 (1976).Google Scholar
  15. 15.
    A. Schweig, N. Thon, S. F. Nelsen, and L. A. Grezzo,J. Am. Chem. Soc.,102, No. 25, 7438 (1980).Google Scholar
  16. 16.
    J. E. Anderson,J. Am. Chem. Soc.,91, No. 23, 6374 (1969).Google Scholar
  17. 17.
    U. Burkert and N. L. Allinger (eds.), ACS Monograph No. 177: Molecular Mechanics, ACS, Washington, DC (1982).Google Scholar
  18. 18.
    V. N. Yandovskii, B. V. Gidaspov, and I. V. Tselinskii,Usp. Khim.,50, No. 2, 296 (1981).Google Scholar
  19. 19.
    I. N. Zyuzin and D. B. Lempert,Izv. Akad. Nauk, Ser. Khim., No. 4, 831 (1985); O. A. Luk'ya, G. A. Smirnov, and A. M. Vasil'ev,Izv. Akad. Nauk, Ser. Khim., No. 9, 2155 (1990).Google Scholar
  20. 20.
    A. Angeli,Gazz. Chim. Ital.,26, No. 1, 7 (1896).Google Scholar
  21. 21.
    V. V. Aleshin, G. N. Shirokova, and V. Ya. Rosolovskii,Zh. Neorg. Khim.,26, No. 8, 2051 (1981).Google Scholar
  22. 22.
    Yu. P. Artsybasheva and B. V. Ioffe,Zh. Org. Khim.,18, No. 9, 1802 (1982).Google Scholar
  23. 23.
    I. G. Zenkevich, V. N. Yandovskii, Yu. P. Artsybasheva, V. S. Kuznetsov, and I. V. Tselinskii,Zh. Org. Khim.,23, No. 1, 3 (1987).Google Scholar
  24. 14.
    G. A. Marchenko, L. F. Chertanova, M. Yu. Antipin, Yu. T. Struchkov, and L. N. Punegova,Dokl. Akad. Nauk,294, No. 5, 1169 (1987).Google Scholar
  25. 25.
    H. Hope and M. R. Sequeira,Inorg. Chem.,12, No. 2, 286 (1973).Google Scholar
  26. 26.
    D. W. H. Rankin, M. R. Todd, F. G. Riddell, and E. S. Turner,J. Mol. Struct.,71, No. 1, 171 (1981).Google Scholar
  27. 27.
    C. H. Chang, R. F. Porter, and S. H. Bauer,J. Am. Chem. Soc.,92, No. 18, 5313 (1970).Google Scholar
  28. 28.
    W. R. Krigbaum, Y. Chatani, and P. G. Barber,Acta Crystallogr. Sect. B,26, No. 2, 97 (1970).Google Scholar
  29. 29.
    E. Kirby,Anomeric Effect of Oxygen-Containing Compounds [Russian translation], Mir, Moscow (1985).Google Scholar
  30. 30.
    V. F. Rudchenko, S. M. Ignatov, and R. G. Kostyanovskii (Kostyanovsky),J. Chem. Soc. Chem. Commun., No. 3, 261 (1990).Google Scholar
  31. 31.
    B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin,The Chemistry of Organic Derivatives of Hydrazine [in Russian], Khimiya, Leningrad (1979), p. 146.Google Scholar
  32. 32.
    D. W. Dixon and R. H. Weiss,J. Org. Chem.,49, No. 23, 4487 (1984).Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • V. F. Rudchenko
  • S. M. Ignatov
  • I. I. Chervin
  • A. É. Aliev
  • M. O. Dekaprilevich
  • Yu. T. Struchkov
  • R. G. Kostyanovskii

There are no affiliations available

Personalised recommendations