Anthracene 1,2-oxide: synthesis and role in the metabolism of anthracene by mammals

Abstract

Synthesis of anthracene 1,2-oxide proceeds in good yield via dehydrobromination of 1 -acetoxy-2,4-dibromo1,2,3,4-tetrahydroanthracene. In contrast, dehydrobromination of 2-acetoxy-3,4-dibromo-1,2,3,4-tetrahydroanthracene produced 1 -bromoanthracene instead of the desired anthracene 2,3-oxide or its oxepin tautomer. Nucleophilic attack of thioethoxide on anthracene 1,2-oxide yields trans-1 -hydroxy-2-ethylthio-1,2-dlhydroanthracene which readily eliminates water with concomitant migration of the thioethoxide group to produce 1 - anthryl ethyl sulphide. In vitro metabolism of anthracene with liver microsomes forms predominantly trans-1,2-dihydroxy-l,2-dihydroanthracene with little evidence of metabolism at the 9,10-position.