7714-98-9Relevant academic research and scientific papers
The oxysulfenylation of alkenes with dimethyl sulfoxide/oxalyl chloride
Liu, Yongguo,Gao, Yang,Wang, Zhitong,Dong, Jian,Ding, Rui,Sun, Baoguo,Tian, Hongyu
supporting information, p. 2662 - 2670 (2019/07/22)
A convenient method for the oxysulfenylation of alkenes using dimethyl sulfoxide/oxalyl chloride is described. Cycloalkenes give trans-adducts stereospecifically. The reactions of styrene are highly regioselective for Markovnikov adducts, whereas aliphati
NH4I-mediated three-component coupling reaction: Metal-free synthesis of β-alkoxy methyl sulfides from DMSO, alcohols, and styrenes
Gao, Xiaofang,Pan, Xiaojun,Gao, Jian,Jiang, Huanfeng,Yuan, Gaoqing,Li, Yingwei
supporting information, p. 1038 - 1041 (2015/03/30)
A novel synthesis recipe for β-alkoxy methyl sulfides was developed via NH4I-mediated three-component oxysulfenylation reaction of styrenes with DMSO and alcohols. This method features simple operation and readily available starting materials, and it provides an alternative sulfenylating agent generated from DMSO for oxysulfenylation reactions.
FORMATION AND REACTIVITY OF THE ADDITION PRODUCTS OF ALKOXIDES AND THIOLATE ANIONS TO VINYL SELENONES
Tiecco, Marcello,Chianelli, Donatella,Tingoli, Marco,Testaferri, Lorenzo,Bartoli, Donatella
, p. 4897 - 4906 (2007/10/02)
Vinyl selenones react with sodium methanethiolate in methanol to give the product of conjugate addition and subsequent displacement of the selenonyl group.On the contrary, the same reaction carried out with alkoxide anions affords the conjugate addition products in excellent yields.These β-alkoxy alkyl phenyl selenones are stable compounds which can react in several ways with loss of the selenonyl group.Their reactions with MeONa or MeSNa have been investigated both in MeOH and in DMF.The products observed derive from substitution and elimination processes as well as from retro Michael reactions followed by nucleophilic substitution of the vinyl selenone thus generated.These results indicate that the ArSeO2 is a strong electron attracting group with peculiar properties.Beside making acidic the α-hydrogen atoms it activates the carbon-carbon double bond towards the addition of anionic reagents and it acts as a good leaving group in nucleophilic substitution, both aliphatic and vinylic, and in elimination reactions.The appropriate choice of the reagent and of the solvent allows to direct the reaction towards the desired products.Useful synthetic applications of these reactions are presented.
Preparation and Reaction of 1-(Methylthio- and phenylthio)vinyllithium Reagents
Takeda, Takeshi,Furukawa, Hiroyuki,Fujimori, Mizue,Suzuki, Kouichi,Fujiwara, Tooru
, p. 1863 - 1869 (2007/10/02)
An improved procedure for the preparation of 1-(methylthio- and phenylthio)vinyllithium reagents utilizing 2-methoxyalkyl sulfides was developed and their reactions with ketones, aldehydes, oxiranes, and alkyl halides were studied.
A CONVENIENT MATHOD FOR PREPARATION OF 1-(METHYLTHIO) AND 1-(PHENYLTHIO)VINYLLITHIUM REAGENTS
Takeda, Takeshi,Furukawa, Hiroyuki,Fujiwara, Tooru
, p. 593 - 596 (2007/10/02)
1-(Methylthio) and 1-(phenylthio)vinyllithiums were prepared by the treatment of the corresponding 2-methoxyethyl sulfides with twice molar amounts of butyllithium in the presence of N,N,N',N'-tetramethylethylenediamine (TMEDA). β-Alkylthio-β,γ-unsaturated alcohols were obtained in good yields by the reaction of the lithium salts with aldehydes.
