The Reactions of O(2) ((1)Delta(g)) with Anancomeric 1,3-Dithianes. The First Experimental Evidence in Support of a Hydroperoxy Sulfonium Ylide as a Precursor to Sulfoxide on the Sulfide Singlet Oxygen Reaction Surface.

@article{Toutchkine1999TheRO,
  title={The Reactions of O(2) ((1)Delta(g)) with Anancomeric 1,3-Dithianes. The First Experimental Evidence in Support of a Hydroperoxy Sulfonium Ylide as a Precursor to Sulfoxide on the Sulfide Singlet Oxygen Reaction Surface.},
  author={Alexei Toutchkine and Edward L. Clennan},
  journal={The Journal of organic chemistry},
  year={1999},
  volume={64 15},
  pages={5620-5625}
}
The kinetic isotope effects for the formation of anancomeric 1,3-dithiane-1-oxides in the reactions of singlet oxygen with the parent 1,3-dithianes have been determined for a series of 2-protio and 2-deuterio analogues. The substantial isotope effects are used to argue for formation of a hydroperoxysulfonium ylide as a key intermediate in sulfoxide… CONTINUE READING