Synthesis and n.m.r. spectra of 2,6- and 2,4-diaryl-3,7-dioxabicyclo-[3.3.0]octanes

Abstract

A series of isomeric 2,6- and 2,4-diaryl-3,7-dioxabicyclo[3.3.0]octanes have been prepared via the corresponding threo, and erythro-dioxo-diesters. Comparison of their ¹H and ¹³C n.m.r. spectra reveals small differences in chemical shifts and coupling constants which could be diagnostic in assigning structures to such compounds. The structure of 4-hydroxysesamin has been confirmed by direct correlation with sesamin.