Ionic hydrogenation of 1-phthaloyl-2-p-substituted benzoylcyclopropanes

  • S. I. Alferova
  • A. V. Kisin
  • G. A. Kudryavtseva
  • L. P. Zalukaev
  • Z. P. Parnes
Organic Chemistry
  • 14 Downloads

Conclusions

  1. 1.

    1-Phthaloyl-2-p-X-substituted benzoylcyclopropanes (where X=F, Cl, Br, OCH3), regardless of the substituent, are selectively reduced by ionic hydrogenation to 1-phthaloyl-2-p-substituted benzylcyclopropanes. As the electronegativity of the substituent decreases, the reduction rate increases.

     
  2. 2.

    The stability of the phthaloyl CO groups and the three-membered ring in this reaction is attributed to their mutual interaction; this agrees well with experimental data and with the13C NMR spectra of the compounds.

     

Keywords

Hydrogenation Experimental Data Rate Increase Reduction Rate Mutual Interaction 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    D. N. Kursanov, Z. N. Parnes, M. I. Kalinkin, and N. M. Loim, Ionic Hydrogenation [in Russian], Khimiya, Moscow (1979).Google Scholar
  2. 2.
    O. K. Popova, N. I. Kopteva, L. P. Zalukaev, S. M. Markosyan, M. I. Kalinkin, Z. N. Parnes, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Ser. Khim., 2084 (1981)Google Scholar
  3. 3.
    N. A. Revina, S. I. Belykh, L. P. Zalukaev, Z. N. Parnes, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Ser. Khim., 2003 (1980).Google Scholar
  4. 4.
    L. F. Johnson and W. C. Jankowski, Carbon 13 NMR Spectra, Wiley-Interscience, New York (1972).Google Scholar
  5. 5.
    E. Breitmeier, G. Haus, and W. Voelter, Atlas of Carbon NMR Data, London (1973).Google Scholar
  6. 6.
    J. B. Stothers, Carbon 13 NMR Spectroscopy, Academic Press, New York (1972).Google Scholar
  7. 7.
    I. K. Anokhina and N. V. Remizova, VINITI Deposit, No. 1746 (1975).Google Scholar
  8. 8.
    N. M. Loim, V. A. Baranova, L. V. Moiseeva, L. P. Zalukaev, Z. N. Parnes, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Ser. Khim., 843 (1974).Google Scholar

Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • S. I. Alferova
    • 1
  • A. V. Kisin
    • 1
  • G. A. Kudryavtseva
    • 1
  • L. P. Zalukaev
    • 1
  • Z. P. Parnes
    • 1
  1. 1.A. N. Nesmeyanov Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

Personalised recommendations