Russian Journal of Organic Chemistry

, Volume 42, Issue 11, pp 1636–1641 | Cite as

Synthesis of 3-oxatricyclo[,7]decene derivatives

  • R. N. Zolotarev
  • M. E. Yakovlev
  • V. V. Razin


Unsaturated haloethers of norpinane structure were prepared by reaction of N-iodo-and N-bromosuccinimides with 1-phenyltricyclo[,7]-heptane in the presence of unsaturated propargyl or allyl alcohol. The iodopropargyloxy derivative underwent reductive 6-exo-cyclization when treated with tributyltin hydride resulting in 5-methylene-3-oxa-2-phenyltricyclo[,7]decane, and the iodoallyloxy derivative on heating in the presence of benzoyl peroxide suffered isomerization into 5-iodomethyl-3-oxa-2-phenyltricyclo[,7]decene. Bromopropargyloxy and bromoallyloxy derivatives failed to undergo the reductive cyclization under the treatment with a system cobaloxime(III)-sodium borohydride, but suffered hydrogenetion at the multiple carbon-carbon bond.


Heptane Sodium Borohydride Benzoyl Peroxide Allyl Alcohol Reductive Cyclization 
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Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • R. N. Zolotarev
    • 1
  • M. E. Yakovlev
    • 1
  • V. V. Razin
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia

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