Reaction of Active Methylene Groups with 1,2-Di(Bromoseleno)Benzene toward Benzo-1,3(2H)-Diselenoles

The 1,2-di(bromoseleno)benzene has been found to be a bifunctional electrophile able to react with C-H acids. The tandem diselenylation of the active methylene group in β-diketones, β-keto- and β-cyanoesters, diethyl malonate, and malonitrile resulted in the ring closure on the carbon atom. Based on...

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Bibliographic Details
Published inSynthetic communications Vol. 35; no. 8; pp. 1077 - 1083
Main Authors Potaczek, Piotr, Kloc, Krystian, Młochowski, Jacek
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 01.04.2005
Taylor & Francis
Subjects
1,2-di(bromoseleno)benzene
1,3-diketones
benzo-1,3(2H)-diselenoles
Chemistry
Chemistry, Organic
diethyl malonate
Physical Sciences
Science & Technology
selenium compounds
diethyl malonate
1,3-diketones
selenium compounds
1,2-di(bromoseleno)benzene
benzo-1,3(2H)-diselenoles
SELENIUM
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Summary:The 1,2-di(bromoseleno)benzene has been found to be a bifunctional electrophile able to react with C-H acids. The tandem diselenylation of the active methylene group in β-diketones, β-keto- and β-cyanoesters, diethyl malonate, and malonitrile resulted in the ring closure on the carbon atom. Based on this reaction, 2,2-disubstituted benzo-1,3(2H)-diselenoles, a new group of selenaheterocycles, were obtained in good yields.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-200054209