7447-11-2Relevant academic research and scientific papers
Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation
Delcaillau, Tristan,Bismuto, Alessandro,Lian, Zhong,Morandi, Bill
, p. 2110 - 2114 (2019/12/24)
A nickel-catalyzed aryl thioether metathesis has been developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.
An efficient rearrangement of secondary alkyl S-methyl xanthates by trimethylaluminum (TMA)
Barton, Derek H. R.,Choi, Seung-Yong
, p. 2695 - 2698 (2007/10/03)
The rearrangement of secondary S-methyl xanthates to S-methyl dithiocarbonates at room temperature using trimethylaluminum has been studied. This reaction affords an efficient and simple method for converting secondary alcohols to thiols.
Metalation of 1,3-Dithiolanes. Mercaptan Synthesis and Carbonyl Transposition
Wilson, Stephen R.,Georgiadis, Gregory M.,Khatri, Hiralal N.,Bartmess, John E.
, p. 3577 - 3583 (2007/10/02)
The reaction of 1,3-dithiolanes with n-butyllithium results in fragmentation to the corresponding thiocarbonyl compound followed by furhter reaction with n-butyllithium.All four types of thiocarbonyl reactions are observed: reduction, S-addition, C-addition, double addition.Synthetic applications of this reaction for the synthesis of secondary mercaptans and 1,2-carbonyl transposition (23 -> 24a-c) are described.
