Advertisement

Chemistry of Heterocyclic Compounds

, Volume 9, Issue 1, pp 26–30 | Cite as

Indoles

XXXIV. O-Phenylhydroxylamine as the o-analog of phenylhydrazine in the Fischer reaction
  • I. I. Grandberg
  • V. I. Sorokin
Article

Abstract

Under the conditions of the Fischer reaction, O-phenylhydroxylamine forms mixtures of isomeric (with respect to substitution in the 2 and 3 positions) benzofurans with methyl ketones. Only 3-substituted 2-methylbenzofurans were isolated when methyl ketones with a “strongly activated” methylene group were used as the carbonyl component.

Keywords

Methyl Organic Chemistry Carbonyl Ketone Indole 
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.
    I. I. Grandberg and N. M. Przheval'skii, Izv. Moskovsk. Sel'skokhoz, Akad. im. K. A. Timiryazeva, 192 (1972).Google Scholar
  2. 2.
    I. I. Grandberg and T. I. Zuyanova, Khim. Geterotsikl. Soedin., 875 (1968).Google Scholar
  3. 3.
    B. Robinson, Chem. Rev., 63, 373 (1963).Google Scholar
  4. 4.
    M. H. Palmer and P. S. McIntyre, J. Chem. Soc., B, No. 4, 446 (1969).Google Scholar
  5. 5.
    T. Sheradsky, Tet. Letters, 5225 (1966).Google Scholar
  6. 6.
    D. Kaminsky, I. Shavel, and R. I. Meltzer, Tet. Letters, 859 (1967).Google Scholar
  7. 7.
    T. Sheradsky, J. Heterocycl. Chem., 4, 413 (1967).Google Scholar
  8. 8.
    A. Mooradian and P. E. Dupont, J. Heterocycl. Chem., 4, 441 (1967).Google Scholar
  9. 9.
    A. Mooradin, Tet. Letters, 407 (1967).Google Scholar
  10. 10.
    L. A. Aksanova, L. M. Sharkova, I. F. Kucherova, and V. A. Zagorevskii, Khim. Geterotsikl. Soedin., 1581 (1970).Google Scholar
  11. 11.
    K. Nakanishi, Infrared Spectra and Structure of Organic Compounds [Russian translation], Mir, Moscow (1965), p. 64.Google Scholar
  12. 12.
    K. H. Pausacker and C. I. Schubert, J. Chem. Soc., 814 (1950).Google Scholar
  13. 13.
    H. Becker, Introduction to the Electronic Theory of Organic Reactions [Russian translation], Mir, Moscow (1965), p. 198.Google Scholar
  14. 14.
    C. L. Bumgardner and R. L. Lilly, Chem. Ind., 539 (1962).Google Scholar

Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1975

Authors and Affiliations

  • I. I. Grandberg
    • 1
  • V. I. Sorokin
    • 1
  1. 1.K. A. Timiryazev Moscow Agricultural AcademyUSSR

Personalised recommendations