A theoretical study of reactivity and regioselectivity in the hydroxylation of adamantane by ferrate(VI).

@article{Shiota2003ATS,
  title={A theoretical study of reactivity and regioselectivity in the hydroxylation of adamantane by ferrate(VI).},
  author={Yoshihito Shiota and Naoki Kihara and Takashi Kamachi and Kazunari Yoshizawa},
  journal={The Journal of organic chemistry},
  year={2003},
  volume={68 10},
  pages={3958-65}
}
The conversion of adamantane to adamantanols mediated by ferrate (FeO(4)(2)(-)), monoprotonated ferrate (HFeO(4)(-)), and diprotonated ferrate (H(2)FeO(4)) is discussed with the hybrid B3LYP density functional theory (DFT) method. Diprotonated ferrate is the best mediator for the activation of the C-H bonds of adamantane via two reaction pathways, in which 1-adamantanol is formed by the abstraction of a tertiary hydrogen atom (3 degrees ) and 2-adamantanol by the abstraction of a secondary… CONTINUE READING