ISSN:
0170-2041
Keywords:
Ozonolysis
;
1,4-Cyclohexadiene
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Ozonolysis of Olefins, I. - Ozonolysis of 1,4-Cyclohexadiene and Acid-Catalysed Reaction of Primary Cleavage ProductsThe 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199019900131
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