DMP制备.pdfVIP

J. Org. Chem. 1993,58, 2899 2899 An Improved Procedure for the Preparation Dess-Martin conditions. Further evidenceforthe sporadic of the Dess-Martin Periodinane behavior of the Dess-Martin acetylation can be found in the literature. Thus, Evans et al. obtained periodinane Robert E. Ireland and Longbin Liu 3by heating a mixture of the hydroxyiodinaneoxide 2 in HOAc/AczO at 80 Conlyuntil dissolutionwas complete Department of Chemistry, University of Virginia, (ca. 10 min). Ayling and co-workers8 found that con- Charlottesville, Virginia 22901 tinuous passage of dry inert gasthrough the reaction head Received December 15, 1992 spacen facilitatesthe acetylation. Dessand Martin pointed out that the rate of acetylation depended on the particle The Dess-Martin periodinane, l,l,l-triacetoxy-1,l- sizes of the hydroxyiodinane oxide 2 and suggested that dihydro-1,2-benziodoxol-3(lH)-one(31, has become the it be monitored for product formation by lH NMR. reagent of choice for the oxidation of primary and By using only a catalytic amount of TsOH in place of secondaryalcoholsto aldehydesandketones,respectively.2 HOAc, we were able to effect the acetylation of the The mild reaction conditions (at room temperature and hydroxyio