84538-93-2Relevant academic research and scientific papers
One-pot Synthesis of Allyl Sulfides from Sulfinate Esters and Allylsilanes through Reduction of Alkoxysulfonium Intermediates
Hosoya, Takamitsu,Kobayashi, Akihiro,Matsuzawa, Tsubasa,Yoshida, Suguru
supporting information, p. 813 - 816 (2020/07/23)
An efficient method to synthesize allyl sulfides from sulfinate esters and allylsilanes is described. Based on the reactivity of isolated allyl(methoxy)phenyl sulfonium triflate, we have developed a simple one-pot method for the allyl sulfide synthesis by S-allylation of sulfinate esters and subsequent reduction with sodium borohydride. A number of allyl sulfides were prepared by this method leaving various functional groups unreacted.
NaI-Mediated Acetamidosulphenylation of Alkenes with Nitriles as the Nucleophiles: A Direct Access to Acetamidosulfides
Zheng, Yang,He, Yue,Rong, Guangwei,Zhang, Xiaolu,Weng, Yuecheng,Dong, Kuiyong,Xu, Xinfang,Mao, Jincheng
, p. 5444 - 5447 (2015/11/18)
An example of a transition-metal-free, direct, and efficient acetamidosulphenylation reaction of alkenes using nitriles as the nucleophiles via a radical process is presented. This reaction shows a broad substrate scope and high regioselectivity and provides straightforward access to acetamidosulfide derivatives in moderate to high yields.
Sulfur mediated allylic C-H alkylation of tri- and disubstituted olefins
Hu, Gang,Xu, Jiaxi,Li, Pingfan
supporting information, p. 6036 - 6039 (2015/01/08)
A novel transition-metal-free, sulfur mediated allylic C-H alkylation reaction through a one-pot procedure involving an ene-like step between simple olefins and activated sulfoxides to generate allylic sulfonium intermediates, and a subsequent [2,3]-sigmatropic rearrangement step under basic conditions to give allylic C-H alkylation products, has been developed. This method is applicable to tri- and disubstituted olefin substrates in both inter- and intramolecular fashions.
Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides
Pace, Vittorio,Castoldi, Laura,Holzer, Wolfgang
supporting information; experimental part, p. 967 - 972 (2012/03/11)
A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.
The Preparation of β-Fluoro Thioethers
Purrington, Suzanne T.,Correa, Itzela D.
, p. 1080 - 1083 (2007/10/02)
Addition of benzenesulfenyl chloride to electron-rich olefins in the presence of silver produces β-fluoro thioethers.The trans adducts could also be prepared from β-chloro thioethers and silver fluoride.
Elimination and Addition Reactions. Part 37. A Comparative Study of Electronic, Steric , and Solvent Effects upon Reactivity in Additions of Benzenesulphenyl Chloride to Alkenes
Jones, G. Alun,Stirling, Charles J. M.,Bromby, Norman G.
, p. 385 - 394 (2007/10/02)
Rates of additions of benzenesulphenyl chloride to 35 alkenes in several solvents have been measured, and the products of the reactions have in most cases been identified.Results for arylalkenes broadly confirm previous work, but the responses to solvent change are not uniform throughout.The reactivity of bridged cycloalkanes is substantially greater than that of cycloalkenes, but that of cyclo-pentadiene dimer is anomalously small.For allylic substrates, the correlation of electron density at the double bond with reactivity is shown by a rectilinear relationship between log k and ?I.Allyl iodide and allyl alcohol are anomalously more reactive than this correlation would predict; this is accounted for by solvation and by internal solvation effects respectively.
METHYLENATION WITH PHOSPHONATE ESTERS
Fox, Marye Anne,Triebel, Carol A.,Rogers, Ralph
, p. 1055 - 1062 (2007/10/02)
A series of 2-aryl-1-thioalkyl-2-propenes have been synthesized by treating the corresponding thioalkylated acetophenones with the anion of methyl phosphonate.
