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

摘要

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