Oxidative ozonolysis of a polyunsaturated fatty acid in BF3–MeOH medium

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Abstract
The ozonolysis of the methyl ester of a typical naturally-occurring polyunsaturated acid (linoleic) in BF3-MeOH medium was investigated. Referring only to difunctional products, yields of the principal reaction product, dimethyl azelate, were approximately 96%. The characteristic secondary product, the dimethyl ester of the acid with 1 less C, was formed only to the extent of 2% or less. Other intermediates and difunctional secondary products which were identified include the C9 methyl half-ester, half-aldehyde and the corresponding dimethyl acetal. Dimethyl malonate was not recovered quantitatively under the conditions employed. Monofunctional products qualitatively and quantitatively duplicated the difunctional products.