21128-72-3Relevant academic research and scientific papers
Transition metal-free formal hydro/deuteromethylthiolation of unactivated alkenes
Chen, Shuangyang,Wang, Jia,Xie, Lan-Gui
supporting information, p. 4037 - 4042 (2021/05/19)
Methylthioether is involved in the methylthiotransfer process in organisms, and therefore its functionality is of paramount importance to living organisms. Several methods for the installation of the methylthio group in small molecules have been reported previously; however, procedures starting from unactivated alkenes are rare. Herein, we report a formal hydro/deuteromethylthiolation of alkenes by using dimethyl(methylthio)sulfonium trifluoromethanesulfonate as the stimulator and sodium borohydride/deuteride as the hydrogen/deuterium source. The process represents a mild, transition metal-free and methanethiol-free route towards the synthesis of methylthioethers from unactivated alkenes. This journal is
Ex Situ Formation of Methanethiol: Application in the Gold(I)-Promoted Anti-Markovnikov Hydrothiolation of Olefins
Kristensen, Steffan K.,Laursen, Simon L. R.,Taarning, Esben,Skrydstrup, Troels
supporting information, p. 13887 - 13891 (2018/10/02)
A protocol for the Au-promoted anti-Markovnikov hydrothiolation of olefins using ex situ generated methanethiol is reported. The use of S-methylisothiourea hemisulfate salt as a solid precursor for methanethiol generation ensures a safe and reliable deliverance of a stoichiometric amount of this thiol. The procedure was shown to work for a broad range of olefins providing the corresponding hydrothiolated adduct in good to excellent yields. Mechanistic evaluations suggest that thiyl radicals are generated and that gold acts as an efficient but stable radical initiator.
Metalation reactions. VIII. Metalation of benzyl methyl sulfide
Cabiddu, Salvatore,Floris, Constantino,Melis, Stefana,Sotgiu, Francesca
, p. 61 - 64 (2007/10/02)
The metalation of benzylmethyl sulfide with n-butyllithium in hexane and in the presence of TMEDA has been investigated.The results show that metalation occurs only at the benzylic position with no wittig type rearrangement, cleavage of thioether bond and
The Lithium Diisopropylamide-induced Fragmentation of 1,3-Dithiolane Derivatives of Several Ketones Having α-Hydrogen
Ikehira, Hideyuki,Tanimoto, Shigeo,Oida, Tatsuo
, p. 2537 - 2538 (2007/10/02)
The reaction of 1,3-dithiolane derivatives of ketones having a-hydrogen with lithium diisopropylamide results in fragmentation to the corresponding thioketone followed by further conversion in a few steps to the other intermediate species which, on trapping with alkyl halide, leads to a vinylic sulfide and/or a sulfide bearing a secondary alkyl group.
