Formolysis and acetolysis of linear saturated and allylic secondary cyclopropyl carbinols

  • B. A. Cheskis
  • N. M. Ivanova
  • A. M. Moiseenkov
Organic Chemistry
  • 30 Downloads

Abstract

Simple esterification of a series of secondary aliphatic cyclopropyl carbinols under the influence of concentrated HCO2H or AcOH without modification of the carbon skeleton is disclosed. Under the same conditions related allyl alcohols undergo stereospecific isomerization to the corresponding esters of 3E,5E-dienols.

Keywords

Alcohol Ester Allyl AcOH Carbon Skeleton 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A. S. Arora and I. K. Ugi, Methoden der Organischen Chemie (Houben-Weyl), E. Müller (ed.), Vol. V/1b, Georg Thieme Verlag, Stuttgart (1972), p. 912.Google Scholar
  2. 2.
    M. Julia, S. Julia, and R. Guegan, Bull. Soc. Chim. Fr., 1072 (1960); M. Julia, M. Caput, and C. Descoins, Bull. Soc. Chim. Fr., 2135 (1965); S. F. Brady, M. A. Ilton, and W. S. Johnson, J. Am. Chem. Soc.,90, 2882 (1968); K. Mori, M. Ohki, A. Sato, and M. Matsui, Tetrahedron,28, 3739 (1972).Google Scholar
  3. 3.
    A. M. Moiseenkov, B. A. Cheskis (Czeskis), N. M. Ivanova, and O. M. Nefedov, Org. Prep. Proc. Int.,22, 215 (1990); B. A. Cheskis, N. M. Ivanova, A. M. Moiseenkov, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2025 (1990).Google Scholar
  4. 4.
    B. A. Cheskis, N. M. Ivanova, A. M. Moiseenkov, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2539 (1990).Google Scholar
  5. 5.
    N. M. Ivanova, B. A. Cheskis, E. V. Rubanova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 640 (1991).Google Scholar
  6. 6.
    A. M. Moiseenkov, B. A. Cheskis (Czeskis), and O. M. Nefedov, Synthesis, 932 (1985); B. A. Cheskis, A. M. Moiseenkov, and O. M. Nefedov, Dokl. Akad. Nauk SSSR,289, 637 (1986).Google Scholar
  7. 7.
    K. Mori, J. Fukami, and T. Ohtaki, Agric. Biol. Chem.,35, 1116 (1971).Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • B. A. Cheskis
    • 1
  • N. M. Ivanova
    • 1
  • A. M. Moiseenkov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations