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Product selectivity in the electroreduction of thioesters

The electroreduction of differently substituted aromatic and aliphatic thioesters (RCOSR′) led to regioselective reactions depending on the nature of the substituents. Thus, the cleavage between the carbonyl group and the SR′ group afforded α-diketones and the cleavage between the RCOS group and the...

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Bibliographic Details
Published in:Tetrahedron 2005-02, Vol.61 (7), p.1709-1714
Main Authors: Weïwer, M., Olivero, S., Duñach, E.
Format: Article
Language:English
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Summary:The electroreduction of differently substituted aromatic and aliphatic thioesters (RCOSR′) led to regioselective reactions depending on the nature of the substituents. Thus, the cleavage between the carbonyl group and the SR′ group afforded α-diketones and the cleavage between the RCOS group and the alkyl R′ group afforded thiocarboxylic acids selectively. Thioester compounds (RCOSR′) undergo highly regioselective cleavage upon electroreduction, depending on the alkyl or aryl nature of the two R and R′ groups. Aromatic α-diketones, aliphatic thioacids or amides can be selectively obtained in moderate to good yields.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.12.050