98626-97-2Relevant articles and documents
Xanthates as Thiol Surrogates for Nucleophilic Substitution with Aryl Halides
Sokolov, Anatolii I.,Mikhaylov, Andrey A.,Baleeva, Nadezhda S.,Baranov, Mikhail S.
, p. 4350 - 4357 (2021/08/24)
We herein report an unprecedented xanthate-based protocol for the preparation of aryl-alkyl thioethers. Heating xanthates with aryl halides and namely cesium carbonate in methanol provides the target thioethers in generally good yields within short reaction times. This method allows one to avoid contact with odorous thiols and also to introduce substituents of which the corresponding thiols are virtually unavailable or inconvenient in use.
TMSCH2Li-LiDMAE: a new nonnucleophilic reagent for C-2 lithiation of halopyridines
Doudouh, Abdelatif,Gros, Philippe C.,Fort, Yves,Woltermann, Christopher
, p. 6166 - 6171 (2007/10/03)
A new superbasic reagent has been discovered by combining TMSCH2Li and LiDMAE in hexane. This reagent was found highly efficient for the C-2 lithiation of sensitive chloro- and fluoropyridines. The metallation occurred chemo- and regioselectively at 0 °C avoiding the nucleophilic addition or substrate degradation commonly obtained with other alkyllithiums even at lower temperatures.
The Reaction of Some Halogenated Pyridine Thioethers and Sulphones with Carbon Disulphide
Dunn, A. D.,Norrie, R.
, p. 269 - 272 (2007/10/02)
Dithiocarboxylation of some halogenated pyridine sulphones with carbon disulphide and sodium hydride leads to the formation of thiomethyl derivatives via Smiles rearrangement of the initially produced dianion, fragmentation and subsequent methylation.In one instance the pyridino-1,4-dithiine 7 was obtained.The thioether 2d was also converted into a thiomethyl derivative when subjected to the same reaction sequence.