Rearrangements of epoxides of some acyclic terpenoids in acidic media

Rearrangements of epoxides of some acyclic terpenoids in acidic media Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2001, Volume: 37, Number: 6, Pages: 793-801 Pages count : 9 DOI: 10.1023/A:1012449228670

Authors

Khomenko T.M. ¹ , Korchagina D.V. ¹ , Barkhash V.A, ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia

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.

Khomenko T.M. , Korchagina D.V. , Barkhash V.A.
Rearrangements of epoxides of some acyclic terpenoids in acidic media
Russian Journal of Organic Chemistry. 2001. V.37. N6. P.793-801. DOI: 10.1023/A:1012449228670 WOS Scopus РИНЦ

Web of science	WOS:000171938500005
Scopus	2-s2.0-0035540355
Elibrary	13369302
OpenAlex	W2998003180