Base-catalyzed isomerization of 3-methyl-3-norcarene epoxides
- 25 Downloads
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
Unable to display preview. Download preview PDF.
- 1.É. Kh. Kazakova, Z. G. Isaeva, and Sh. S. Bikeev, Izv. Akad. Nauk SSSR, Ser. Khim.,1979, 2330.Google Scholar
- 2.R. P. Thummel and B. Rickborn, J. Am. Chem. Soc.,92, 2064 (1970).Google Scholar
- 3.H. Kuczynski and K. Marks, Rocz. Chem.,43, 943 (1969).Google Scholar
- 4.G. Teutsch and R. Bucourt, Chem. Commun.,18, 763 (1974).Google Scholar
- 5.Z. Rykowski and K. Burak, Rocz. Chem.,50, 1709 (1976).Google Scholar
- 6.H. Gilman and R. G. Jones, Org. React.,6, 339 (1951).Google Scholar