Highly efficient sulfimidation of 1,3-dithianes by Cu(I) complexes
A series of four Cu(I) complexes were tested for sulfimidation of 1,3-dithianes in the presence of [N-(p-tolysulfonyl)imino]phenyliodinane (PhI=NTs) as the nitrene-transfer agent. Cu(TMPhen)(PPh3)Br is an efficient catalyst with more than 90% yield of the
Giribabu,Singh, Surya P.,Patil, Nandkumar M.,Kantam, M. Lakshmi,Gupte, Sunil P.,Chaudhari, Raghunath V.
p. 619 - 625
(2008/04/12)
Electronic effect, steric hindrance, and anchimeric assistance in oxidation of sulphides. Neighbouring-group participation through Sulphur-oxygen nonbonded interaction
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.
Ruff, Ferenc,Kucsman, Arpad
p. 1123 - 1128
(2007/10/02)
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