Efficient, Solvent-Free Oxidation of Organic Compounds with Potassium Dichromate in the Presence of Lewis Acids.docVIP

Molecules 2001, 6, 900-908 molecules ISSN 1420-3049 Efficient, Solvent-Free Oxidation of Organic Compounds with Potassium Dichromate in the Presence of Lewis Acids Iraj Mohammadpoor-Baltork*, Majid M. Sadeghi and Abol-Hassan Adibi Department of Chemistry, Isfahan University, Isfahan 81744, Iran, Fax: (+98) 311 6689732. * Author to whom correspondence should be addressed; e-mail: imbaltork@sci.ui.ac.ir Received: 9 August 2001; in revised form 25 September 2001 / Accepted: 22 October 2001 / Published: 31 October 2001 Abstract: The synthetic utility of potassium dichromate in the presence of Lewis acids under solid phase conditions is described. This reagent efficiently oxidizes alcohols, acyloins, oximes and semicarbazones to their corresponding carbonyl compounds, while trimethylsilyl and tetrahydropyranyl ethers, ethylene acetals and ketals undergo oxidative deprotection to produce carbonyl compounds efficiently. Keywords: Oxidation, Organic compounds, Dichromate, Lewis acids, Solvent-free conditions. Introduction The total syntheses of complex molecules demand new methods in different areas of organic chemistry. Therefore, the development of reagents is always rewarding to synthetic organic chemistry. Oxidation is one of the most important classes of organic reactions from different points of view and effecting them under non-aqueous and aprotic conditions has found valuable applications in modern organic syntheses [1]. Potassium dichromate has been used extensively for the oxidation of different organic compounds under varied aqueous acidic conditions [1-6], but some of these methods suffer from disadvantages such as high reaction temperature, overoxidation of primary alcohols to carboxylic acids, long reaction times, low yields of the products and tedious workup. Its use as an oxidant under neutral conditions is also limited by its very low solubili