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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 (CC BY 3.0).
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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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