Selective rearrangements of 4a,5-epoxides of 4,4-dimethyl-1,2,3,4,6,8a-hexahydronaphthalenes. |
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| Authors: | Steven P Tanis Yousef M Abdallah Paul G Williard |
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| Institution: | Department of Chemistry Michigan State University East Lansing, Michigan 48824 U.S.A.;Department of Chemistry Brown University Providence, Rhode Island 02912 U.S.A. |
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| Abstract: | Epoxidation selectivity of a number of 4,4-dimethyl-1,2,3,4,6,8a-hexahydronaphthalenes 4 were examined. Exposure of the isolated α-epoxides 7provided excellent yields (79–92%) or rearranged fused indene-oxetanes 8. Treatment of β-epoxides 5 with BF3·OEt2 also yields oxetanes 8 and related alcohols 9 and 10. |
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