Tetrahedron

Experimental and Computational Studies on Substituent Effects in Reactions of Peracid–Aldehyde Adducts

C Lehtinen, V Nevalainen, G Brunow

Index: Lehtinen, Christel; Nevalainen, Vesa; Brunow, Goesta Tetrahedron, 2000 , vol. 56, # 47 p. 9375 - 9382

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Citation Number: 27

Abstract

Liquid phase oxidation of six branched and four linear aldehydes by dioxygen and m- chloroperbenzoic acid was studied experimentally. 2-Substituted (α-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 ...