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Molecules 2004, 9(3), 117-124; doi:10.3390/90300117
Article

Kinetics of the Epoxidation of Geraniol and Model Systems by Dimethyldioxirane

* , ,  and
Department of Chemistry, Center for Biotech and Drug Design, Georgia State University, Atlanta, Georgia 30303-3083, USA
* Author to whom correspondence should be addressed.
Received: 5 February 2004 / Accepted: 12 February 2004 / Published: 28 February 2004
(This article belongs to the Special Issue Biologically Relevant Heterocyclic Compounds)
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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.
Keywords: Mono-epoxidation; selectivity Mono-epoxidation; selectivity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Baumstark, A.L.; Franklin, P.J.; Vasquez, P.C.; Crow, B.S. Kinetics of the Epoxidation of Geraniol and Model Systems by Dimethyldioxirane. Molecules 2004, 9, 117-124.

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