Ozonolyse von Olefinen, I. Ozonolyse von 1,4-Cyclohexadien und säurekatalysierte Folgereaktionen von Primärspaltprodukten

✍ Scribed by Mittelbach, Martin ;Poklukar, Norbert ;Junek, Hans

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 398 KB
• Volume: 1990
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199019900131

✦ Synopsis

Ozonolysis of Olefins, I. — Ozonolysis of 1,4‐Cyclohexadiene and Acid‐Catalysed Reaction of Primary Cleavage Products

The reaction of 1,4‐cyclohexadiene (1) with ozone under different reaction conditions was investigated. Complete ozonolysis of 1 in chloroform led to a highly explosive ozonide. Oxidative ozonolysis gave malonic acid in 30% yield, ozonolysis in alcoholic solutions of HCl gave alkyl 3,3‐dialkoxypropionates 3 in 60–70% yield and small amounts of the 1,1,3,3‐tetraalkoxypropane 4 as well as dialkyl malonate 5. Partial ozonolysis of 1 in HCl/methanol led to a mixture of 3, 5, and the corresponding (Z)‐3‐hexene derivatives 6a–c. Depending on the reaction time and concentration of HCl, also the two methanol addition products 7b and 7d could be obtained. To verify the structure of these two compounds, 4‐methoxycyclohexene (8) was ozonized in HCl/methanol, which gave a mixture of 7a–d.