Säurekatalysierte Umlagerungen von 1, 5??Dimethyl??6??methyliden??tricyclo [3.2. 1.02, 7] oct??3??en??8endo??olen

G Mukherjee??Müller, P Gilgen, J Zsindely…

Index: Mukherjee-Mueller,G. et al. Helvetica Chimica Acta, 1977 , vol. 60, p. 1758 - 1780

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Citation Number: 5

Abstract

Summary The tricyclic alcohols 2, 3, 4 and 6 (Scheme I) are synthesized by the reaction of the tricyclic ketone 1 with sodiumborohydrid or metalloorganic reagents. Their configuration at C (8) is determined by NMR. in the presence of Eu (fod),. The exo-attack of 1 by the nucleophil forming the endo-alcohol is favored, the n-electrons of C (3)= C (4) hindering the endo-attack. On treatment with sulfuric acid in dioxane/water at 25" the tertiary alcohols ...