114597-44-3Relevant academic research and scientific papers
Geminal Selectivity in Singlet Oxygen Reactions
Clennan, Edward L.,Chen, Xiangning
, p. 3124 - 3125 (1988)
Replacement of a hydrogen on tetramethylethylene with a variety of functional groups produces a family of substrates which react preferentially with singlet oxygen by abstraction of a geminal hydrogen to form allylic hydroperoxides.
Temperature, Solvent, and Substituent Effects on the Singlet Oxidations of Allylic Phenyl Sulfoxides, Sulfones, and Sulfides
Clennan, Edward L.,Chen, Xiangning
, p. 8212 - 8218 (2007/10/02)
The reaction of singlet oxygen with a series of allylic sulfoxides, sulfones, and sulfides have been examined as a function of extent of reaction, temperature, and solvent.Hydroperoxy groups but not alkyl, hydrogen, or hydroxyl on chiral carbons β to sulfide sulfur induce diastereoselective sulfoxide formations.Evidence is presented that suggests that the oxidation at sulfur occurs with anchimeric assistance from the hydroperoxy group via a favorable sulfurane-like transition state.
