Separation and spectral data of the six isomeric ozonides from methyl oleate.

The structures of the products obtained on ozonation of methyl oleate have been re-examined. The assignments for the six isomeric ozonides of methyl oleate have been made by 1H and 13C nuclear magnetic resonance (NMR), which were consistent with the retention times observed in high-performance liquid chromatography; the assignments were confirmed by mass and infrared spectroscopy. Two triplets for the ozonide ring protons of the cis and trans isomers in the normal (MOO1) and the two cross ozonides (MOO1 and MOO3) can be resolved by 400 MHz NMR. For MOO1 and MOO3, where the two ring carbons are equivalent, two peaks for the ring carbons of each cross ozonides are resolved in the 13C NMR spectra, one for the cis and one for the trans isomer. For MOO2, four peaks for the ring carbons are resolved in the 13C NMR spectra, two for the cis and two for the trans isomer.