Journal
TETRAHEDRON
Volume 68, Issue 4, Pages 1105-1108Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.11.083
Keywords
Allylic oxidation; Olefins; Kharasch-Sosnovsky reaction; Simplex; Multivariate optimization
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Funding
- Junta de Andalucia
- Universidad de Cadiz
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The multivariate optimization method known as simplex is applied to the Kharasch-Sosnovsky allylic oxidation of double bonds. By applying this method, the amounts of three variables (copper source, oxidant, and additive) are optimized at the same time. Under the conditions thus obtained the reaction takes place in a considerable shorter time, being the alkene the limiting reagent. These conditions are applied to some monoterpenes and sesquiterpenes leading regioselectively to the corresponding benzoate esters, opening a route to the employment of this reaction in the synthesis of more complex molecules. (C) 2011 Elsevier Ltd. All rights reserved.
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