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Hydrogen Peroxide Oxidation of Naphthalene Derivatives Catalyzed by Poly(bis-1,2-diphenylene) Diselenide

Giurg M., Syper L., Młochowski J.

Polish Journal of Chemistry

2004

Vol. 78 / nr 2

231--248

Oxidation of 1- and 2-substituted naphthalenes (1) with 30% hydrogen peroxide in the presence of poly(bis-1,2-diphenylene) diselenide (PPDS) has been investigated. Depending on the substrate used trans-2-carboxycinnamic acid (2), and its isomer, (1-oxo-1,3-dihydroisobenzofuran-1-yl)acetic acid (3) or 2-naphthoic acid (4b) was a major product. Oxidation of hydroxynaphthalenes 1b and 1c is a convenient way to obtain trans-2-carboxy cinnamic acid (2) in almost quantitative yield. The mechanism of the reaction is postulated.