Journal
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Volume 28, Issue 10, Pages 619-628Publisher
WILEY-BLACKWELL
DOI: 10.1002/poc.3462
Keywords
aromatic ring hydroxylation; Baeyer-Villiger oxidation; multivariate regression; oxidation mechanisms; response surface methodology; statistical experimental design
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Funding
- Department of Chemistry at University of Bergen
- Department of Chemistry, Materials and Chemical Engineering at Politecnico di Milano
- Faculty of Mathematics and Natural Sciences at University of Bergen
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Peroxy acids can be used as the terminal oxidant for the Baeyer-Villiger oxidation of acetophenones and for direct ring hydroxylation of methoxy-substituted benzenes. An oxidative system involving 3-chloroperbenzoic acid (mCPBA) and 2,6-dimethoxyacetophenone as model substrate was investigated by means of statistical experimental design, multivariate modelling and response surface methodology. The outcome of the organic peracid oxidation experiments was portrayed by a multi-response matrix consisting of the yields of three different compounds; 2,6-dimethoxyphenyl acetate, 1-(4-hydroxy-2,6-dimethoxy-phenyl) ethanone and 3-hydroxy-2,6-dimethoxy-phenyl acetate. The optimized reaction protocol was utilized to investigate a series of various substituted acetophenones. The overall investigation revealed that both the molecular structure of the acetophenone substrate and the experimental conditions exhibited a substantial impact on whether the oxidation reaction follows the oxygen insertion or direct ring hydroxylation mechanism. An improved protocol for the direct ring hydroxylation was also obtained from the experimental and modelling described herein. Copyright (C) 2015 John Wiley & Sons, Ltd.
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