The protoberberine → spirobenzylisoquinoline → dibenzocyclopent[b]azepine rearrangement

Abstract

Dihydroprotoberberine salts 5, 10, and 14, rearrange in base to the spirobenzylisoquinolines 8, 12, and 16, respectively. But the dihydroprotoberberine salt 18, which does not possess a phenolic function in ring D, rearranges to the dibenzocyclopent[b]azepine 21 through the intermediacy of the aziridinium ion 20. © 1973.