Synthesis and spontaneous racemization of benz[a]anthracene 1,2-oxide
Abstract
Benz[a]anthracene 1,2-oxide (1,2-epoxy-1,2-dihydrobenz[a]anthracene), a minor metabolite of benz[a]anthracene in hepatic systems, has been synthesized both from racemic precursors and from separated diastereoisomeric bromohydrin esters whose absolute stereochemistry has been determined by n.m.r. methods. The benz[a]anthracene 1,2-oxide obtained was racemic as previously predicted from PMO calculations.