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

30 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

Access to Document

10.1016/S0040-4020(01)00754-2

Cite this

@article{92678e5a98284c379173b8f3bc45bb44,

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

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}",

note = "Funding Information: We are grateful to the National Science Council of the ROC for financial support (Grant No. NSC-88-2113-M-006-006). ",

year = "2001",

month = sep,

day = "10",

doi = "10.1016/S0040-4020(01)00754-2",

language = "English",

volume = "57",

pages = "7829--7837",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "37",

}

TY - JOUR

T1 - Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds

AU - Tsai, An I.

AU - Wu, Yi Lung

AU - Chuang, Che Ping

N1 - Funding Information: We are grateful to the National Science Council of the ROC for financial support (Grant No. NSC-88-2113-M-006-006).

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.

UR - http://www.scopus.com/inward/record.url?scp=0035840114&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035840114&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)00754-2

DO - 10.1016/S0040-4020(01)00754-2

M3 - Article

AN - SCOPUS:0035840114

VL - 57

SP - 7829

EP - 7837

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 37

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this