- Pd-Catalyzed aerobic oxidation of the sesquiterpene isolongifolene: A green and heterogeneous process
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The oxidation of the sesquiterpene isolongifolene, catalyzed by Pd/SiO2 prepared through a conventional sol–gel method, resulted mainly in isolongifolen-9-one (65% selectivity), a compound which occupies a prominent place in perfume industry. In addition to the product obtained from the allylic oxidation of isolongifolene, the formation of other oxygenated products with potential industrial application (both total yield of 94%) was also observed. The system can be used for oxidation of other sesquiterpene, valencene. In this case, it was possible to obtain oxygenated products with up to 66% yield. The reactions occurred under mild conditions in a green and heterogeneous oxidation catalytic system. Pd (II) was used as a solo catalyst in the absence of co-oxidants. The catalyst can be easily recovered and re-used maintaining activity and selectivity.
- Nunes de Melo, Carla,Robles-Azocar, Patrícia Alejandra,Rodrigues, Yuri Blanc
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- Cobalt-catalyzed oxidation of terpenes: Co-MCM-41 as an efficient shape-selective heterogeneous catalyst for aerobic oxidation of isolongifolene under solvent-free conditions
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Cobalt-containing MCM-41 was used as a heterogeneous catalyst for the liquid-phase aerobic oxidation of isolongifolene, one of the most available sesquiterpenes. The material was prepared by direct incorporation of cobalt into the framework through the hy
- Robles-Dutenhefner, Patricia A.,da Silva Rocha, Kelly A.,Sousa, Edesia M.B.,Gusevskaya, Elena V.
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experimental part
p. 72 - 79
(2009/09/25)
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- Synthesis in fluorous phase: A convenient synthesis of isolongifolene epoxide and its rearrangement to ketone
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Aerobic epoxidation of isolongifolene 1 with pivalaldehyde/oxygen in perfluoro-2-butyltetrahydrofuran (FC-75) in the presence of Mn(OAc)3·2H2O as catalyst yielded isolongifolene-epoxide 3 in good yield. The rearrangement of isolongifolene-β-epoxide to ketone 4 was achieved.
- Ravikumar,Bégué, Jean-Pierre,Bonnet-Delpon, Danièle,Ourévitch, Michèle
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- Structure Elucidation of Oxidation-Reduction Products of Isolongifolene
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Three alcohol isomers have been synthesized in high yield from isolongifolene to provide easy-to-make and cheap odorants.Oxidation of isolongifolene by reaction with m-chloroperbenzoic acid yielded a mixture of the corresponding epoxide, ketone, and alcoh
- Bombarda, Isabelle,Smadja, Jacqueline,Gaydou, Emile M.,Conan, Jacques-Yves,Faure, Robert
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p. 138 - 142
(2007/10/02)
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- Chromic Acid Oxidation of Some Oxiranes
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Oxiranes derived from some alkenes, with olefinic bonds present in different stereoelectronic environments, have been treated with Cr(VI)-reagents.The major products obtained have been identified and their formation rationalized.In some cases, the method becomes synthetically useful for C-C bond cleavage.
- Krishna, R. R.,Chawla, H. P. S.,Dev, Sukh
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p. 1190 - 1196
(2007/10/02)
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