Kinetics of the Epoxidation of Geraniol and Model Systems by Dimethyldioxirane
Author(s): A. L. Baumstark | P. J. Franklin | P. C. Vasquez | B. S. CrowJournal: Molecules ISSN 1420-3049
Volume: 9; Issue: 3; Start page: 117; Date: 2004;
Original page
Keywords: Mono-epoxidation | selectivity
ABSTRACT
The mono-epoxidation of geraniol by dimethyldioxirane was carried out invarious solvents. In all cases, the product ratios for the 2,3 and 6,7 mono-epoxides werein agreement with literature values. Kinetic studies were carried out at 23 oC in thefollowing dried solvent systems: acetone (k2 = 1.49 M-1s-1), carbon tetrachloride/acetone(9/1, k2=2.19 M-1s-1), and methanol/acetone (9/1, k2 = 17 M-1s-1). Individual k2 valueswere calculated for epoxidation of the 2,3 and 6,7 positions in geraniol. The non-conjugated diene system was modeled employing two simple independent alkenes:2-methyl-2-pentene and 3-methyl-2-buten-1-ol by determining the respective k2 valuesfor epoxidation in various solvents. The kinetic results for each independent alkeneshowed that the relative reactivity of the two epoxidation sites in geraniol as a function ofsolvent was not simply a summation of the independent alkene systems.
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