Investigations on the synthesis and chemiluminescence of novel 2-coumaranones

被引：23

作者：

Schramm, Stefan ^{[1
]}

Weiss, Dieter ^{[1
]}

Navizet, Isabelle ^{[2
,3
]}

Roca-Sanjuan, Daniel ^{[4
]}

Brandl, Herbert ^{[1
]}

Beckert, Rainer ^{[1
]}

Goerls, Helmar ^{[1
]}

机构：

[1] Univ Jena, Inst Organ Chem & Makromol Chem, Humboldtstr 10, D-07743 Jena, Germany

[2] Univ Witwatersrand, Inst Mol Sci, Sch Chem, ZA-2050 Johannesburg, South Africa

[3] Univ Paris Est, Lab Modelisat & Simulat Multi Echelle, MSME UMR 8208, CNRS, F-77454 Marne La Vallee, France

[4] Uppsala Univ, Dept Chem Angstrom, Theoret Chem Programme, S-75002 Uppsala, Sweden

来源：

ARKIVOC | 2013年

基金：

新加坡国家研究基金会;

关键词：

Chemiluminescence; dioxetanone; 2-coumaranone; Tscherniac-Einhorn reaction; ACYL-ALPHA-ARYLGLYCINES; AMIDOALKYLATION;

D O I：

10.3998/ark.5550190.0014.314

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optimized syntheses of 2-coumaranone derivatives and, based thereon, several new representatives of this class of substances are described. They show a clearly visible chemiluminescence under the exposure of a strong base and in the presence of oxygen. The wavelength and intensity of the light emitted depends on both the substituents on the benzo annealed, as well as on the type of base used. A mechanism is presented in which a delocalized enolate is postulated as a key intermediate.

引用

页码：174 / 188

页数：15

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