Synthesis of a sym-oxepin oxide with restricted conformational mobility and altered reactivity. X-Ray crystal and molecular structure of 4,7-dibromo-3a,7a:5,6-diepoxyperhydroindene

Abstract

Nitrogen extrusion from the azo diepoxide (4) generates the sym-oxepin oxide (5a), the altered reactivity of which is attributed to the conformational rigidity of (5a) as compared to the parent molecule (2); bromination of the bridgehead diene (5a) gives the dibromo-diepoxide (8) whose structure has been verified by X-ray crystal structure analysis.