Issue 4, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Observations on the origin of phenylacetaldehyde in styreneepoxidation and the mechanism of oxidations catalysed by manganese complexes of porphyrins

António M. d'A. Rocha Gonsalves*a  and  Arménio C. Serrab  

* Corresponding authors

a Departamento de Química, Universidade de Coimbra, Rua Larga, 3000 Coimbra, Portugal

b Universidade Católica Portuguesa, R. Dr. Mendes Pinheiro, 24, 3080 Figueira da Foz, Portugal

Abstract

Phenylacetaldehyde (PhA) has been observed as a by-product in H2O2 metalloporphyrin catalytic oxidation of styrene. We have found that the mechanism of these oxidations depends on the relative amount of the carboxylic acid that is used as co-catalyst. With an excess of the organic acid less PhA is formed due to the intervention of metalloacylperoxo species (1) instead of a metallo-oxo species (2). Whatever the conditions used, the PhA which is formed comes chiefly from styrene oxide (SO) isomerization. This process seems to be due to the presence of oxygen centered radicals formed through metalloporphyrin reaction with hydrogen peroxide.

Graphical abstract: Observations on the origin of phenylacetaldehyde in styrene epoxidation and the mechanism of oxidations catalysed by manganese complexes of porphyrins

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Article information

DOI
https://doi.org/10.1039/B201033J
Article type
Paper
Submitted
07 Aug 2001
Accepted
28 Jan 2002
First published
18 Feb 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 715-719

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Observations on the origin of phenylacetaldehyde in styrene epoxidation and the mechanism of oxidations catalysed by manganese complexes of porphyrins

A. M. d'A. Rocha Gonsalves and A. C. Serra, J. Chem. Soc., Perkin Trans. 2, 2002, 715 DOI: 10.1039/B201033J

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