37527-79-0Relevant academic research and scientific papers
NEIGHBOURING-GROUP PARTICIPATION IN THE OXIDATION OF SULPHIDES WITH HYDROGEN PEROXIDE
Ruff, Ferenc,Kucsman, Arpad
, p. 241 - 246 (2007/10/02)
Using a set of sulphides (o- and p-XC6H4SMe), the electronic effect, steric hindrance and anchimeric assistance for the O-transfer by H2O2 have been investigated by a kinetic method.The steric effect and anchimeric assistance were evaluated by comparing t
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.
