Rearrangements of Epoxides of Some Acyclic Terpenoids in Acidic Media |
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Authors: | T. M. Khomenko D. V. Korchagina V. A. Barkhash |
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Affiliation: | (1) Siberian Division, Russian Academy of Sciences, Vorozhtsov Novosibirsk Institute of Organic Chemistry, Novosibirsk, 630090, Russia |
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Abstract: | 2,3-Epoxygeraniol undergoes dissimilar rearrangements in contact with liquid superacids at low temperature or on solid superacids at room temperature due to different location of the arising cationic center depending on the superacid character. 2,3-Epoxynerol, 6,7-epoxycitronellol, and 6,7-geranyl acetate on ZrO2SO42- afford the corresponding ketones via epoxy ring opening followed by 1,2-hydride shift. With 6,7-geranyl acetate 7-oxanobornane formed as a minor product. The mode of generation of the cationic center (either the olefin protonation or the epoxy ring opening) affects the rearrangement direction at similar conditions. |
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