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The chemical reactivity of some terpenes investigated by alumina catalyzed epoxidation with hydrogen peroxide and by DFT calculations

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons58928

Rinaldi,  Roberto
Instituto de Química, Universidade Estadual de Campinas, P.O. Box 6154, 13083-970 Campinas-SP, Brazil;
Research Group Rinaldi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Zitation

Silva, J., Vinhado, F., Mandelli, D., Schuchardt, U., & Rinaldi, R. (2006). The chemical reactivity of some terpenes investigated by alumina catalyzed epoxidation with hydrogen peroxide and by DFT calculations. Journal of Molecular Catalysis A, 252, 186-193. doi:10.1016/j.molcata.2006.02.042.


Zitierlink: http://hdl.handle.net/11858/00-001M-0000-0024-21B0-D
Zusammenfassung
The selectivity of the alumina catalyzed epoxidation of (S)-limonene, citronelal, citral, citronelol and (1S)-(α)-pinene with aqueous 70 wt% and anhydrous 24 wt% hydrogen peroxide is described. DFT molecular orbital calculations were used aiming at a better understanding of the reactivity of these terpenes. The more nucleophilic carbon–carbon double bond, which has a higher molecular orbital energy, is preferentially epoxidized (site-selectivity). Furthermore, a preference for epoxidation in competition with other possible reactions is observed for citronelal, citral, citronelol and (1S)-(α)-pinene (chemo-selectivity). Nonetheless, we were not able to achieve a stereo-selective epoxidation of the terpenes using alumina and hydrogen peroxide.