Abstract
Biomimetic hydroxylation using several oxo-iron systems was applied to bencyclane (I) in order to examine the correlation between the nature of the active species and the distribution of the oxidized products. Aromatic hydroxylation was found to occur predominantly in the ferrous ion-H2O2 system containing a ligand such as phenol or catechol, whereas regioselective aliphatic hydroxylation was observed in the ferrous ion-H2O2 system with detergent or cyclodextrin. The ferrous ion-H2O2 system with cyclodextrin was found to produce the bencyclane cycloheptane ring-hydroxylated metabolite (IIγ-cis) with fairly good regio-and stereoselectivity.
