109845-78-5Relevant articles and documents
A concerted addition mechanism in [Hmim]Br-triggered thiol-ene reactions: a typical “ionic liquid effect” revealed by DFT and experimental studies
Feng, Lin,Ye, Renlong,Yuan, Tao,Zhang, Xiao,Lu, Guo-ping,Zhou, Baojing
, p. 5752 - 5758 (2019)
A concerted one-step addition mechanism for anti-Markovnikov hydrothiolation in [Hmim]Br catalyzed thiol-ene reactions is revealed by a combined DFT and experimental study for the first time. This special mechanism represents a typical “ionic liquid effec
Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water
Lin, Ya-Mei,Lu, Guo-Ping,Wang, Gui-Xiang,Yi, Wen-Bin
, p. 382 - 389 (2017/04/26)
A newly developed aqueous system with acid and phosphide was introduced in which odorless and stable sodium arylsulfinates can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents, and metals.
Intramolecular assistance of electron transfer from heteroatom compounds. Electrochemical oxidation of 2-(2-pyridyl)ethyl-substituted ethers, sulfides, and selenides
Watanabe, Mitsuru,Suga, Seiji,Yoshida, Jun-Ichi
, p. 243 - 247 (2007/10/03)
Organoheteroatom compounds having a 2-(2-pyridyl)ethyl group were synthesized and their oxidation potentials were determined by rotating disk electrode voltammetry. The oxidation potentials were found to be less positive than those of the corresponding compounds having a phenyl group in place of the pyridyl group. The dynamic coordination of the pyridyl group to the heteroatom, which stabilizes the cation radical intermediate, seems to be responsible for facilitating the electron transfer. The magnitude of the intramolecular assistance increases along with an increase in the oxidation potential of the parent compounds. This tendency can be explained in terms of the energy match between the nonbonding p orbital of the pyridyl nitrogen and the HOMO of the parent heteroatom compound.