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Paper | Regular issue | Vol 43, No. 10, 1996, pp.2215-2221
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7553
Oxidative Free Radical Reaction of 2-Phenylthio-1,4-naphthoquinones Initiated by Manganese(III) Acetate

Che-Ping Chuang and Sheow-Fong Wang

*Department of Chemistry, Natioanl Cheng Kung University, Tainan, 70101, Taiwan, R.O.C.

Abstract

A free radical reaction between 2-phenylthio-1,4-naphothoquinines and diethyl malonate initicated by manganese(III) acetate is described. This free tadical reaction provides a new method for the synthesis of 6,11-dihydro-6,11-dioxo-12H-5-thianaphthacenes. This reaction was performed in various solvents, the best results were obtained in DMSO. With meta substituent on phenylthio ring, this reaction shows unusual high regioselectivity.