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 in:Synthetic communications 2005-04, Vol.35 (8), p.1077-1083
Main Authors: Potaczek, Piotr, Kloc, Krystian, Młochowski, Jacek
Format: Article
Language:English
Subjects:
1,2-di(bromoseleno)benzene
1,3-diketones
benzo-1,3(2H)-diselenoles
diethyl malonate
selenium compounds
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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