114129-35-0Relevant academic research and scientific papers
Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
Zhao, Bin,Hammond, Gerald B.,Xu, Bo
, (2021/09/13)
We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.
Electronic effect, steric hindrance, and anchimeric assistance in oxidation of sulphides. Neighbouring-group participation through Sulphur-oxygen nonbonded interaction
Ruff, Ferenc,Kucsman, Arpad
, p. 1123 - 1128 (2007/10/02)
Using a set of sulphides o- and p-XC6H4SMe, the electronic effect, steric hindrance, and anchimeric assistance for electrophilic Cl+ addition by TsNHCI and O-transfer by NalO4 were investigated by a kinetic method. The steric effect and anchimeric assistance of the ortho-substituents were evaluated by comparing the reactivity of ortho- and para-substituted compounds (K = ko/kp). For neighbouringgroup activity the following order was obtained: CH2OH ~ CH2OMe ~ CH2CO2Me CH2CO2H ~ CH2NMe2 CH2C02 - ~ CHO CO2Me ~ CO2H COMe ~ CONH2 C02- Reaction rates show that the anchimeric assistance is governed by an S mellip; 0 or S ... N close contact developed in the transition state between oppositely polarized heteroatoms. Factors controlling neighbouringgroup participation through attractive non-bonded interactions are discussed.
