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Oxidation of menthone oxothiolane

  • A. V. TimshinaEmail author
  • S. A. Rubtsova
  • I. N. Alekseev
  • M. I. Kodess
  • E. G. Mamochkina
  • P. A. Slepukhin
  • A. V. Kuchin
Article

meta-Chloroperoxybenzoic acid (m-ClPBA) was shown to be an oxidant for two stereoisomers of menthone oxothiolane. The effect of steric factors on the ability to oxidize the sulfide group was found. Oxidation of (5S,6S,9R)-6-isopropyl-9-methyl-1-oxo-4-thiaspiro[4.5]-decane to the sulfone was prevented by the steric proximity of an isopropyl group to the S atom in the oxothiolane ring.

Key words

menthone oxothiolane stereoisomers sulfoxide oxidation of menthone oxothiolane 

Notes

Acknowledgment

The work was supported by the RF President (Program for Support of Leading Scientific Schools, Grant NSh-4028.2008.3).

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Copyright information

© Springer Science+Business Media, Inc. 2008

Authors and Affiliations

  • A. V. Timshina
    • 1
    Email author
  • S. A. Rubtsova
    • 1
  • I. N. Alekseev
    • 1
  • M. I. Kodess
    • 2
  • E. G. Mamochkina
    • 2
  • P. A. Slepukhin
    • 2
  • A. V. Kuchin
    • 1
  1. 1.Institute of Chemistry, Komi Scientific Center, Ural BranchRussian Academy of SciencesSyktyvkarRussia
  2. 2.I. Ya. Postovskii Institute of Organic Synthesis, Ural BranchRussian Academy of SciencesEkaterinburgRussia

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