Deazetation of a bicyclic azo compound: resolution of a stereochemical ambiguity and conformational analysis of a biradical

Abstract

Development of a new approach has permitted a fuller analysis of the stereochemistry of deazetation of the stereospecifically deuteriated azo compound (1d) than could be achieved previously, in that it has proved possible to analyse [1,8-²H₂]octa-1,7-diene for E,E-, E,Z,-and Z,Z- content. This has given results for the thermal and photochemical reactions that can be rationalised in terms of partial conformational equilibration of the biradical.