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

The ozonolysis of the methyl ester of a typical naturally-occurring polyunsaturated acid (linoleic) in BF 3 –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 one less carbon, was formed only to the extent of 2% or less. Other intermediates and difunctional secondary products which have been identified include the C 9 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.