کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
68989 | 48527 | 2006 | 8 صفحه PDF | دانلود رایگان |

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.
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 for 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 oxidized and a preference for the epoxidation in competition with other possible reactions is observed.Figure optionsDownload high-quality image (103 K)Download as PowerPoint slide
Journal: Journal of Molecular Catalysis A: Chemical - Volume 252, Issues 1–2, 1 June 2006, Pages 186–193