33451-45-5Relevant academic research and scientific papers
Reactions of Sulfoxides with Magnesium Amides. Transformations of Sulfoxides into Sulfides, Dithioacetals and Vinyl Sulfides
Kobayashi, Kazuhiro,Kawakita, Masataka,Yokota, Kouichi,Mannami, Tohru,Yamamoto, Koji,et al.
, p. 1401 - 1408 (1995)
The reactions of sulfoxides with magnesium amides generated in situ from the reaction of ethylmagnesium bromide and seconday amines, such as diisopropylamine (DIPA) or 2,2,6,6-tetramethylpiperidine (TMP) in diethyl ether, were examined.Diaryl sulfoxides were heated with the diisopropylaminomagnesium reagent in diethyl ether to give the corresponding diaryl sulfides in 42-52percent yields.Sulfoxides bearing hydrogens at the α-position only(RSOCH2R1) reacted with the tetramethylpiperidinomagnesium reagent at room temperature to produce the corresponding dithioacetals (RSCHR1SR) in 47-86percent yields.The treatment of sulfoxides bearing hydrogens both at the α-and β-positions (RSOCHR1CHR2R3) with the magnesium amides at room temperature afforded the corresponding vinyl sulfides (RSCR1=CR2R3) in 52-72percent yields accompanying 2.3-27percent yields of the corresponding dithioacetals.The pathways leading to the products involving the formation of the sulfur-stabilized carbonium ion intermediates are discussed.
Br?nsted Acid-Assisted Zinc-Catalyzed Markovnikov-Type Hydrothiolation of Alkenes Using Thiols
Taniguchi, Nobukazu
, p. 6528 - 6534 (2020/07/14)
The zinc-catalyzed regioselective hydrothiolation of alkenes with thiols was achieved in the presence of 4-toluenesulfonic acid. Through this procedure, Markovnikov-type sulfides were synthesized in excellent yields, and the formation of anti-Markovnikov-
An expeditious and efficient bromomethylation of thiols: Enabling bromomethyl sulfides as useful building blocks
Silva-Cuevas, Carolina,Paleo, Ehecatl,León-Rayo, David F.,Lujan-Montelongo, J. Armando
, p. 24654 - 24659 (2018/07/25)
A facile and highly efficient method for the bromomethylation of thiols, using paraformaldehyde and HBr/AcOH, has been developed, which advantageously minimizes the generation of highly toxic byproducts. The preparation of 22 structurally diverse α-bromomethyl sulfides illustrates the chemo-tolerant applicability while bromo-lithium exchange and functionalization sequences, free radical reductions, and additions of the title compounds demonstrate their synthetic utility.
Copper-catalyzed selective syntheses of Markovnikov-type hydrothiolation products and thioacetals by the reactions of thiols with alkenes bearing heteroatoms
Xi, Hui,Ma, Enlu,Li, Zhiping
, p. 4111 - 4116 (2016/07/06)
Catalyst-controlled divergent reactions of thiophenols with alkenes bearing heteroatoms have been developed. Markovnikov-type hydrothiolation products and thioacetals were synthesized selectively by switching copper catalysts.
