The oxidation of cyclobutanols and aromatic rings with ruthenium tetroxide

✍ Scribed by Joseph A. Caputo; Richard Fuchs

• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 153 KB
• Volume: 8
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)89591-5

✦ Synopsis

The oxidation of organic compounds with ruthenium tetroxide was first reported by Djerassi,' who oxidized sulfides to sulfoxides and sulfones, phenanthrene to phenanthraquinone, and found that ether, benzene, and pyridine are oxidized, whereas carbon tetrachloride, chloroform, alkanes, water, ketones, and esters are relatively inert. Rylander' noted the oxidation of secondary alcohols to ketones, primary alcohols to aldehydes and carboxylic acids, ethers to esters, amides to imides, alkenes to aldehydes, aldehydes to acids, and alkylbenzenes,l-nitronaphthalene, azo compounds, acetylenes, and amines to unidentified products. A useful procedure introduced3 in the oxidation of pyrene to the 4,5-and 1,6-quinones consists in using sodium periodate to reoxidize to the tetroxide ruthenium dioxide formed by the tetroxide-substrate reaction. This