Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds

An I. Tsai; Yi Lung Wu; Che Ping Chuang

doi:10.1016/S0040-4020(01)00754-2

Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds

An I. Tsai, Yi Lung Wu, Che Ping Chuang

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

Abstract

Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds are described. Electrophilic carbon-centered radicals produced by the manganese(III) acetate or cerium(IV) ammonium nitrate oxidation of β-dicarbonyl compounds undergo efficient addition to a C-C double bond of quinone ring. This free radical reaction provides a novel method for the synthesis of naphthacene-5,12-diones.

Original language	English
Pages (from-to)	7829-7837
Number of pages	9
Journal	Tetrahedron
Volume	57
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4020(01)00754-2
Publication status	Published - 2001 Sep 10

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds are described. Electrophilic carbon-centered radicals produced by the manganese(III) acetate or cerium(IV) ammonium nitrate oxidation of β-dicarbonyl compounds undergo efficient addition to a C-C double bond of quinone ring. This free radical reaction provides a novel method for the synthesis of naphthacene-5,12-diones.",

author = "Tsai, {An I.} and Wu, {Yi Lung} and Chuang, {Che Ping}",

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AU - Tsai, An I.

AU - Wu, Yi Lung

AU - Chuang, Che Ping

PY - 2001/9/10

Y1 - 2001/9/10

N2 - Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds are described. Electrophilic carbon-centered radicals produced by the manganese(III) acetate or cerium(IV) ammonium nitrate oxidation of β-dicarbonyl compounds undergo efficient addition to a C-C double bond of quinone ring. This free radical reaction provides a novel method for the synthesis of naphthacene-5,12-diones.

AB - Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds are described. Electrophilic carbon-centered radicals produced by the manganese(III) acetate or cerium(IV) ammonium nitrate oxidation of β-dicarbonyl compounds undergo efficient addition to a C-C double bond of quinone ring. This free radical reaction provides a novel method for the synthesis of naphthacene-5,12-diones.

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JF - Tetrahedron

SN - 0040-4020

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