114597-51-2Relevant academic research and scientific papers
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.
Reactions of an Allylic Sulfide, Sulfoxide, and Sulfone with Singlet Oxygen. The Observation of a Remarkable Diastereoselective Oxidation
Clennan, Edward L.,Chen, Xiangning
, p. 5787 - 5792 (2007/10/02)
The reactions of singlet oxygen with 1--2,3-dimethyl-2-butene (6), 1--2,3-dimethyl-2-butene (7), and 2,3-dimethyl-2-butenyl p-methylphenyl sulfide (8) have been examined.The formation of transient intermediates and products in the reaction of 8 have been followed as a function of extent of reaction and a remarkable diastereoselective reaction has been uncovered.The implications of this discovery for the mechanism of sulfide oxidation is discussed.
