Selective rhenium-catalyzed oxidation of secondary alcohols with methyl sulfoxide in the presence of ethylene glycol, a convenient one-pot synthesis of ketals

Authors
Arterburn, JB Perry, MC
Citation
Jb. Arterburn et Mc. Perry, Selective rhenium-catalyzed oxidation of secondary alcohols with methyl sulfoxide in the presence of ethylene glycol, a convenient one-pot synthesis of ketals, ORG LETT, 1(5), 1999, pp. 769-771
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
5
Year of publication
1999
Pages
769 - 771
Database
ISI
SICI code
1523-7060(19990909)1:5<769:SROOSA>2.0.ZU;2-1
Abstract
[GRAPHICS] Secondary alcohols are oxidized preferentially by DMSO and the catalyst ReO Cl3(PPh3)(2) in the presence of ethylene glycol and refluxing toluene, prod ucing the corresponding ketals. The reactions are rapid, and proceed in ver y good to excellent yields. The byproducts of the reaction, methyl sulfide and water, are easily removed. No epoxidation or other common side reaction s were observed. This direct oxidative transformation of alcohols to the pr otected ketal derivatives should have broad synthetic applicability.