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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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Published in: | Tetrahedron 2005-02, Vol.61 (7), p.1709-1714 |
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Main Authors: | , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/j.tet.2004.12.050 |