Über die Autoxidation von Vinylcylopentan, Vinylcyclohexan und 4-Vinylcyclohex-1-en

✍ Scribed by R. Biela; Dr. W. Bilas; Dr. U. Ihsan; Prof. Dr. W. Pritzkow; Dr. W. Schmidt-Renner

• Publisher: John Wiley and Sons
• Year: 1983
• Tongue: English
• Weight: 381 KB
• Volume: 325
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19833250603

✦ Synopsis

Autoxidation of Vinylcyclopentane, Vinylcyclohexane, and 4‐Vinylcyclohex‐1‐ene

The title olefins were oxidized with molecular oxygen at 75–80°C. About 40% of the oxygen absorbed were found by iodometric titration as peroxidic oxygen. The reaction products were analyzed by a combination of chemical methods, gas chromatography, and ^13^C‐n.m.r.‐spectroscopy.

Vinylcyclopentane and vinylcyclohexane are attacked preferably at the tertiary allylic C‐H‐bonds giving almost equimolar mixtures of the corresponding allylisomeric hydroperoxides. In the case of 4‐vinylcyclohex‐1‐ene the C‐H‐bonds in position 6 are preferably attacked, but products of attack on the other allylic C‐H‐bonds also could be identified.

In all cases the amount of products which could not be detected gaschromatographically was determined by balance experiments in the presence of an internal standard.