Journal
TETRAHEDRON
Volume 56, Issue 47, Pages 9375-9382Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00908-X
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Liquid phase oxidation of six branched and four linear aldehydes by dioxygen and m-chloroperbenzoic acid was studied experimentally. 2-Substituted (alpha -branched) aldehydes reacted to give formates (via Bayer-Villiger mechanism) whereas the related linear saturated aldehydes were converted to the corresponding carboxylic acids. Formation of both these products can be rationalized via rearrangement reactions of peracid-aldehyde adducts 1. Computational studies employing DFT methods at the DNPP level with the Spartan program (v5.0) were carried out in order to understand properties of those adducts. Conformational properties of the adducts 1 were found to shed Light on the differences observed in the reactions of linear and branched adducts. (C) 2000 Elsevier Science Ltd. All rights reserved.
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