The Proton Magnetic Resonance Spectra of some Chlorinated Polycyclodiene Pesticide Metabolites. Rapid Assessment of Stereochemistry

Abstract

The rapid and accurate determination of the relative stereochemistry of some postulated chlorinated polycyclodiene pesticide metabolites without excessive dependence on chemical methods is described. Proton assignments were made employing the new nuclear magnetic resonance (n.m.r.) shift reagent, Eu(DPM)3, which effected the separation of superimposed signals in these systems. The assignments based on coupling constant information and requiring spin decoupling equipment are in good agreement with those obtained from the Eu(DPM)3 studies. The data presented establishes the relative stereochemistry of these biologically important compounds and demonstrates the utility of one or both approaches in elucidating their overall structures.