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Rearrangements of epoxides of some acyclic terpenoids in acidic media

Rearrangements of epoxides of some acyclic terpenoids in acidic media. Khomenko, T. M.; Korchagina, D. V.; Barkhash, V. A. (Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk 630090, Russia). Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), 37(6), 793-801 (English) 2001 MAIK Nauka/Interperiodica Publishing. CODEN: RJOCEQ. ISSN: 1070-4280. DOCUMENT TYPE: Journal CA Section: 30 (Terpenes and Terpenoids) 2,3-Epoxygeraniol undergoes dissimilar rearrangements in contact with liq. superacids at low temp. or on solid superacids at room temp. 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 was 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. Keywords rearrangement epoxide acyclic monoterpenoid superacid epoxynerol epoxycitronellol geranyl acetate rearrangement acidic media Index Entries Terpenes, preparation epoxy; rearrangements of some acyclic monoterpenoid epoxides in acidic media Superacids Monoterpenes rearrangements of some acyclic monoterpenoid epoxides in acidic media Rearrangement catalysts superacids; rearrangements of some acyclic monoterpenoid epoxides in acidic media Epoxides terpenoid; rearrangements of some acyclic monoterpenoid epoxides in acidic media 1314-23-4, uses 7664-93-9, uses 7789-21-1 13637-84-8 106-22-9 106-24-1 1786-07-8 5392-40-5 1564-98-3 50727-94-1 71030-55-2 87575-34-6 390368-69-1 24286-47-3 84560-01-0 87575-36-8 161521-29-5 389860-72-4 389860-73-5 389860-74-6 389860-75-7 rearrangements of some acyclic monoterpenoid epoxides in acidic media