Journal
TETRAHEDRON
Volume 69, Issue 10, Pages 2268-2275Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.01.034
Keywords
Aldehyde; Oxidation; Fragrance; Peracid; Hydroperoxide; Mechanism
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The oxidative degradation of fragrant aldehydes by molecular oxygen has been investigated. The oxygen consumption was monitored and the bond dissociation energy (BDE) of the aldehyde C(O)-H bond were calculated by DFT method. The oxidation products were identified by GC/MS. The different pathways accounting for the oxidative degradation are discussed. The main product is the acid, beside the formate ester. Both oxidation products result from the Baeyer-Villiger reaction involving a peracid R(CO)OOH whereas minor products arise from the hydroperoxide ROOH intermediate derived either from the acyl peroxy radical, R(CO)OOH or from the decarboxylation of the peracid RC(O)OOH. (C) 2013 Elsevier Ltd. All rights reserved.
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