Advertisement

Reaction of 1-hydroxy-5-phenyltetrazole with olefin oxides

  • O. A. Luk'yanov
  • N. I. Shlykova
  • Yu. A. Strelenko
Brief Communications
  • 25 Downloads

Conclusions

  1. 1.

    1-Hydroxy-5-phenyltetrazole adds to ethylene oxide and propylene oxide to give the products of O- and N-β-oxyalkylation in 2∶1 ratio.

     
  2. 2.

    Propylene oxide is opened by 1-hydroxy-5-phenyltetrazole predominantly at the sterically most available carbon atom; this direction is favored by a 3∶1 ratio.

     
  3. 3.

    The product of the O-β-oxyalkylation of 1-hydroxy-5-phenyltetrazole upon treatment with a strong base regenerates the initial N-hydroxytetrazole and, thus, the O-β-hydroxyalkyl-ation of N-hydroxytetrazoles may serve to protect the N-hydroxyl group in these compounds.

     

Keywords

Oxide Ethylene Propylene Carbon Atom Olefin Oxide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    O. A. Luk'yanov and N. I. Shlykova, Izv. Akad. Nauk SSSR, Ser. Khim., 181 (1984).Google Scholar
  2. 2.
    J. Plenkiewicz, Tetrahedron Lett., 399 (1978).Google Scholar

Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • O. A. Luk'yanov
    • 1
  • N. I. Shlykova
    • 1
  • Yu. A. Strelenko
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations