51954-48-4

Upstream product

• 119561-09-0 2,3-Dimethyl-2-butenyl p-methylphenyl sulfide 
• 563-79-1 2,3-Dimethyl-2-butene 
• 5072-70-8 1-bromo-2,3-dimethyl-2-butene 

Downstream Products

• 123358-77-0 2-Methyl-3-(toluene-4-sulfinylmethyl)-but-3-en-2-ol 
• 122145-17-9 (R)-2,3-Dimethyl-1-((R)-toluene-4-sulfinyl)-but-3-en-2-ol 
• 122145-17-9 (S)-2,3-Dimethyl-1-((R)-toluene-4-sulfinyl)-but-3-en-2-ol 
• 114597-50-1 2-Methyl-3-(toluene-4-sulfinylmethyl)-but-3-en-2-yl-hydroperoxide 
• 114597-51-2 (R)-2,3-Dimethyl-1-((R)-toluene-4-sulfinyl)-but-3-en-2-yl-hydroperoxide 
• 114597-51-2 (R)-2,3-Dimethyl-1-((S)-toluene-4-sulfinyl)-but-3-en-2-yl-hydroperoxide 

Relevant academic research and scientific papers

Reactions of an Allylic Sulfide, Sulfoxide, and Sulfone with Singlet Oxygen. The Observation of a Remarkable Diastereoselective Oxidation

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.

Temperature, Solvent, and Substituent Effects on the Singlet Oxidations of Allylic Phenyl Sulfoxides, Sulfones, and Sulfides

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.