Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in situ.

@article{Wong2003InvestigationOT,
  title={Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in situ.},
  author={Man-Kin Wong and N Chung and Lan He and Xue-chao Wang and Zheng Yan and Y Tang and Dan Yang},
  journal={The Journal of organic chemistry},
  year={2003},
  volume={68 16},
  pages={6321-8}
}
We found that dioxiranes generated in situ from ketones 1-6 and Oxone underwent intramolecular oxidation of unactivated C-H bonds at delta sites of ketones to yield tetrahydropyrans. From the trans/cis ratio of oxidation products 1a and 2a as well as the retention of the configuration at the delta site of ketone 5, we proposed that the oxidation reaction… CONTINUE READING