Journal of the American Chemical Society

Tricyclo [5.3. 0.01, 6] decan-5-one and tricyclo [5.4. 0.01, 6] undecan-5-one. Synthesis and selective transformation to spiro and fused bicyclic systems

JF Ruppert, JD White

Index: Ruppert, John F.; White, James D. Journal of the American Chemical Society, 1981 , vol. 103, # 7 p. 1808 - 1813

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Citation Number: 19

Abstract

Abstract: The title compounds (10 and 11) were prepared by copper-catalyzed intramolecular cycloaddition of cyclopentenyl (8) and cyclohexenyl (9) diazo ketones. Reduction of 10 and 11 with lithium in ammonia gave spiro compounds 12 and 14 while exposure to HCI gave chloro ketones 13 and 15. In contrast, acid-catalyzed methanolysis of 10 and 11 afforded fused bicyclic structures 16 and 17. Solvolysis of endo and ex0 ...

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