883-21-6Relevant academic research and scientific papers
Hydrogen peroxide oxidation of naphthalene derivatives catalyzed by poly (bis-1,2-diphenylene) diselenide
Giurg,Syper,Mlochowski
, p. 231 - 238 (2007/10/03)
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.
Behavior of naphthoyloxyl and methoxynaphthoyloxyl radicals generated from the photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones
Najiwara, Toshihiro,Hashimoto, Ji-ichiro,Segawa, Katsunori,Sakuragi, Hirochika
, p. 575 - 585 (2007/10/03)
1-Naphthoyloxyl and 2-naphthoyloxyl radicals were generated from photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones in acetonitrile. The difference in product distribution between the precursors is ascribed to the contribution of the two-bond cleavage in the peroxide decomposition in the singlet state. A series of methoxynaphthoyloxyl radicals were also generated from the corresponding (methoxynaphthoyloxy)pyridones and their behavior was compared with that of unsubstituted naphthoyloxyl radicals. The introduction of a methoxy group in the naphthalene ring stabilizes the naphthoyloxyl radicals to prevent their decarboxylation completely and reduces remarkably their reactivities in the addition to olefins and hydrogen-atom abstraction. The structure of the naphthoyloxyl radicals was discussed on the basis of their absorption spectra and MO calculations.
