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Acceleration of the Dess-Martin Oxidation by Water

Stephanie D. Meyer and Stuart L. Schreiber

*Howard Hughes Medical Institute, Center for Chemical Methodology and Library Development (CMLD-HU) & Broad Institute of Harvard and MIT, Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, Email:

S. D. Meyer, S. L. Schreiber, J. Org. Chem., 1994, 59, 7549-7552.

DOI: 10.1021/jo00103a067


Partial hydrolysis of DMP or incomplete acetylation gives a more effective oxidant, explaining why impure samples of DMP in many cases provide better results than the pure reagent. When reliable and convenient rate enhancement is desired, pure DMP may be decomposed with an equivalent of water immediately before or during its use.

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proposed partial hydrolysis of DMP

Key Words

Dess-Martin Oxidation, Dess-Martin Periodinane

ID: J72-Y1994-220