Die Herstellung von 3, 5-disubstituierten Cyclopentenen durch Ozonolyse von Norbornadien

✍ Scribed by C. A. Grob; H. R. Pfaendler

• Publisher: John Wiley and Sons
• Year: 1970
• Tongue: German
• Weight: 308 KB
• Volume: 53
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19700530828

✦ Synopsis

Abstract

The ozonization of norbornadiene is described. Oxidation of the intermediate with silver oxide furnishes 4‐cyclopentene‐cis‐1, 3‐dicarboxylic acid, reduction with sodium borohydride cis‐1, 3‐bis‐hydroxymethylcyclopent‐4‐ene. The latter was converted to cis‐3, 5‐dimethylcyclopentene by reduction of the corresponding bis‐tosylate with LiAlH~4~. Hydrogenation of the ozonization intermediate over palladium‐lead carbonate (Lindlar's catalyst) afforded 4‐cyclopentene‐cis‐1, 3‐dialdehyde. This reaction represents a new and selective method for the reduction of unsaturated ozonization intermediates.