THE OXIDATION OF ADAMANTANE WITH AN IRON SALEN COMPLEX MODELLING ω-HYDROXYLASE

Article abstract of DOI:10.1016/0040-4039(80)80131-6

An interesting regioseletivity (high secondary selectivity) was observed in the oxidation of adamantane in the presence of (FeSalen)₂O, 2-mercaptoethanol, pyridine, and oxygen, giving 1-adamantanol (67 percent based on the catalyst used), 2-adamantanol (162 percent) and 2-adamantanone (51 percent) for a typical example.The yield of each product was dependent on the reaction conditions especially on the mercaptan concentration.This high secondary selectivity (product ratio, 3.2 : 1) and the predominant formation of 2-adamantanol is unique and quite different from those (ca 1 : 1 mostly adamantanone/1-adamantanol) of autoxidation.This is the first successful ω-hydroxylase model.