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Report | Regular issue | Vol 22, No. 1, 1984, pp.101-106
Published online, 1st January, 1970
DOI: 10.3987/R-1984-01-0101
An Approach to the Mechanism of Photooxidation of Berberine under Basic Conditions

M. Leonor Contreras,* Sergio Rivas, and Roberto Rozas

*Department of Chemistry, Facluty of Science, University of Santiago of Chile, Casilla 56559, Santiago-2, Chile

Abstract

The unsensitized photooxidation of berberine (1) catalyzed by basic reagents such as -SC6H13, -N3, Et3N, -OCH3 or -OC2H5, in solution, is described. As a possible mechanism, the formation of an initial berberine-oxygen exciplex followed by a nucleophilic attack to intermediate (3) and rearrangement of this compound to dioxetane (4) is proposed taking in consideration the new isolated lactamic aldehyde structures (2a) and (2b) from the bulk of the reaction. The intervention of both singlet oxygen and the dihydroberberine (5) in these reactions is disregarded.