Stereoisomer Formation on the Ozonization of Esters of Monounsaturated Fatty Acids.

by Rieche et al. (1). These compounds are also referred to as monomeric ozonides, but this terminology appears to be a misnomer. Hence, the term ozonide is used for “true ozonides” in the present study. During the course of our studies, Schroder (2 ) reported the formation of cisand trans-isomeric ozonides on the ozonization of cis-di-t-butylethylene. Only the trans-isomer was detected on the ozonization of transdi-t-butylethylene, however. Identification of the stereoisomers was made on the basis of gas-liquid chromatography (GLC), relative rates of reduction by LiAlH4, and infrared spectral analysis. I n our study, the formation of cisand trans-ozonides was observed on the ozonization of a number of methyl esters of monounsaturated fatty acids. Cisand trans-ozonides were isolated from both cisand trans-