Base-catalyzed isomerization of 3-methyl-3-norcarene epoxides
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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.
KeywordsEther Epoxy Pyridine Epoxide Main Product
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