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Russian Journal of Organic Chemistry

, Volume 45, Issue 6, pp 810–814 | Cite as

Synthesis and some transformations of (−)-carveol

  • R. F. Valeev
  • N. S. Vostrikov
  • M. S. Miftakhov
Article

Abstract

Reduction of the oxo group in (−)-carvone with LiAlH4, NaBH4, and (i-Bu)2AlH was performed. It was found that the reduction with the system CeCl3 · 7 H2O-NaBH4 in methanol at 20°C is the most practical procedure for the synthesis of (−)-carveol. Solvolysis of (−)-carvyl methanesulfonate gave products of SN2 and SN2′ replacement of the methylsulfonyloxy group, the latter slightly prevailing. Overman rearrangement of (−)-carveol resulted in the formation of the corresponding trichloroacetamide derivative, and intramolecular iodoetherification of the title compound afforded 6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene.

Keywords

Petroleum Ether Solvolysis Carvone Carveol Methanesulfonyl Chloride 
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.

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Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • R. F. Valeev
    • 1
  • N. S. Vostrikov
    • 1
  • M. S. Miftakhov
    • 1
  1. 1.Institute of Organic Chemistry, Ufa Research CenterRussian Academy of SciencesUfaRussia

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