A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions.

ABSTRACT: Treatment of benzanthrone (1) with biphenyl-2-yl lithium leads to the surprisingly stable enol 4, which is converted by dehydrogenation into the benzanthrone derivative 7. Under acidic conditions 4 isomerises to the spiro compound 11 and the bicyclo[4.3.1]decane derivative 12. Furthermore, the formation of 7 and the hydrogenated compound 13 is observed. A mechanism for the formation of the reaction products is proposed and supported by DFT calculations.

SUBMITTER: Debeaux M 

PROVIDER: S-EPMC2707016 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature