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Synlett 1990; 1990(6): 347-348
DOI: 10.1055/s-1990-21089
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Radical Mediated Oxidations in Organic Chemistry; 2. The Direct Preparation of Esters from Aldehydes

István E. Markó* , Abdelaziz Mekhalfia, W. David Ollis
  • *Department of Chemistry, The University, Sheffield, S3 7HF, England
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Publication Date:
08 March 2002 (online)

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Mechanistic investigations of the N-bromosuccinimide oxidation of trimethylsilyl ethers (preceding paper) catalyzed by 2,2′-azobisisobutyronitrile are described. Based on the proposed mechanism, a highly efficient and versatile preparation of mixed esters from aliphatic and aromatic aldehydes and aliphatic trimethylsilyl ethers has been discovered. Aromatic aldehydes require the presence of a catalytic amount of trimethylsilyl triflate to give the mixed esters directly.

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