Kinetics of the Epoxidation of Geraniol and Model Systems by Dimethyldioxirane

Kinetics of the Epoxidation of Geraniol and Model Systems by Dimethyldioxirane

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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 concave roller 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 Foot Pad in geraniol as a function ofsolvent was not simply a summation of the independent alkene systems.