123331-76-0Relevant articles and documents
Ozonolysis of Olefins, I. - Ozonolysis of 1,4-Cyclohexadiene and Acid-Catalysed Reaction of Primary Cleavage Products
Mittelbach, Martin,Poklukar, Norbert,Junek, Hans
, p. 185 - 188 (2007/10/02)
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 30percent yield, ozonolysis in alcoholic solutions of HCl gave alkyl 3,3-dialkoxypropionates 3 in 60-70percent yield and small amounts of the 1,1,3,3-tetraalkoxypropane 4 as well as dialkyl malonate 5.Partial ozonolysis of1 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.