Base-catalyzed isomerization of 3-methyl-3-norcarene epoxides

  • É. Kh. Kazakova
  • S. V. Andreeva
Brief Communications


A study was made of the isomerization of the trans- and cis-3,4-epoxy~3-methylnorcaranes by Et2NLi in ether and t-BuOK in pyridine. The action of both bases on the trans-epoxide gives comparable amounts of 4α-hydroxy-3-methyl-2-norcarene and 3α-hydroxy-3-methyl-4-norcarene. In the reactions of the cis-epoxide the composition of the reaction mixture depends on the employed reagent: in the presence of Et2NLi the main product is 4β-hydroxy-3-methylnorcarane, while with t-BuOK it is 3β-hydroxy-3-methyl-4-norcarene.


Ether Epoxy Pyridine Epoxide Main Product 
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Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • É. Kh. Kazakova
    • 1
  • S. V. Andreeva
    • 1
  1. 1.A. E. Arbuzov Institute of Organic and Physical ChemistryKazan Branch of the Academy of Sciences of the USSRUSSR

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