Decomposition of linoleic acid hydroperoxides by radicals - I. Structures of products of methyl 13-hydroperoxy-cis, traps-9,11-octadecadienoate

Methyl 13-hydroperoxy-cis,trans-9,11-octa-decadienoate (LMPO) was incubated with di-t-butyl peroxyoxalate for 3 h at 38 °C. In the presence of oxygen LMPO decomposed to numerous products among which were methyl 13-oxo-trans,trans-9,11- and methyl 9-oxo-trans,trans-10,12-octadecadienoate, methyl 13-oxo-trans-9,10-epoxy-trans-11-and methyl 9-oxo-trans-12,13-epoxy-trans-10-octadecenoate, methyl 9-hydroxy-trans-12,13-epoxy-trans-10-and methyl 13-hydroxy-trans-9,10-epoxy-trans-11-octadecenoate. Flushing the reaction system with nitrogen reduced the breakdown of LMPO and altered the reaction route in such a manner that a dimethyloctadecadienoate peroxide appeared as the major product.