Rearrangements of Verbenol Epoxide in Supercritical Fluids
, E-ISSN: 1551-7012
||Isomerization, Isopropyl alcohol, Supercritical carbon dioxide, Terpenoid, Verbenol epoxide
Volcho Konstantin P.
Ilʹina Irina V.
Salakhutdinov Nariman F.
Anikeev Vladimir I.
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Prosp. Akad. Lavrent'eva 9
Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, Prosp. Akad.
Lavrent’eva 5, Novosibirsk 630090, Russian Federation
Transformations of verbenol epoxide in a supercritical mixture of CO 2, isopropyl alcohol, and water were studied. The main identified products were similar to those obtained in the presence of Montmorillonite clays, but with much shorter contact times and without an acid catalyst. The reactivity of verbenol epoxide in supercritical media differs dramatically from the behavior of this epoxide in the presence of Lewis acid ZnBr 2. In contrast to studies of α-pinene epoxide transformations, the presence of water caused no essential changes in product distribution. The presence of triethylamine suppressed the rearrangements; obviously the reaction has cationic character.