Organic reactions at alumina surfaces. V. Highly selective alcohol and diol oxidation reactions on alumina

✍ Scribed by Gary H. Posner; Randolph B. Perfetti; Alphonse W. Runquist

• Book ID: 104212931
• Publisher: Elsevier Science
• Year: 1976
• Tongue: French
• Weight: 224 KB
• Volume: 17
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71341-4

✦ Synopsis

Eeceived in USA 16 March 1976; received in UK for publication 10 hguut 1976) We have recently reported that 2-propanol on dehydrated chromatographic alumina converts aldehydes into alcohols and selectively reduces some keto aldehydes into the corresponding keto alcohols (eq. l).lb We report now that the opposite process, oxidation of secondary alcohols, can be performed heterogeneously within the micropores of the solid alumina; trichloroacetaldehyde on dehydrated chromatographic alumina transforms structurally diverse secondary alcohols into ketones and selectively oxidizes some diols into the corresponding keto alcohols (eq. 1). After trying various carbonyl compounds as hydride acceptors, we found trichloroacetaldehyde (and in some cases benzaldehyde) to be the oxidant of choice mainly because product work-up and purification were easiest with this reagent. The general oxidation procedure is as follows.