80865-93-6Relevant academic research and scientific papers
NH4I-Promoted and H2O-Controlled Intermolecular Bis-sulfenylation and Hydroxysulfenylation of Alkenes via a Radical Process
He, Runfa,Chen, Xiuwen,Li, Yibiao,Liu, Qiang,Liao, Chunshu,Chen, Lu,Huang, Yubing
, p. 8750 - 8758 (2019/08/30)
An NH4I-promoted and H2O-controlled intermolecular difunctionalization of alkenes for the synthesis of bis-methylsulfane and β-hydroxysulfides is presented. Mechanistic investigation revealed the reaction proceeds via methylthiyl radical addition to C=C of alkenes to give a carbon-centered radical and immediately cyclize to a thiiranium ion, followed by combination with H2O to afford β-hydroxysulfides in 52-89% yields with chemo- and regioselectivities. In the absence of water, 1,2-disulfenylation takes place to give bis-methylsulfane in moderate to good yields.
β-Substituted Organolithium Compounds from Chlorohydrins: Application to the Direct Synthesis of Bifunctionalized Organic Cpmpounds
Barluenga, Jose,Florez, Josefa,Yus, Miguel
, p. 3019 - 3026 (2007/10/02)
The reaction of different chlorohydrins with n-butyl-lithium at -78 deg C followed by metallation wiht lithium naphthalenide at the same temperature leads to very reactive organolithium compounds bearing an alkoxide function at the β-position with respect to metal.The reaction of these intermediates with several electriphiles leads to mono- as well as bi-functionalized organic compounds.Thus, treatment of these dianions with deuterium oxide, oxygen, carbon dioxide, benzyl bromide, dimethyl disulphide, and carbonyl compounds, gave 2-deuterioalcohols, 1,2-diols, β-hydroxy-acids, 2-benzyl alcohols, 2-hydroxy-thioethers, and 1,3-diols respectively.The preparation of β-substituted organolithium derivatives can be alternatively carried out starting from α-chloroketones by the same procedure.When the lithium atom is linked to a secondary carbon atom the dianions are very unstable and decompose, even at -100 deg C, by β-elimination yielding the corresponding olefins.
β-Substituted Organolithium Compounds. Reaction with Alkyl Halides, Dimethyl Disulfide, and Imines
Barluenga, Jose,Fananas, Francisco J.,Villamana, Jorge,Yus, Miguel
, p. 1560 - 1564 (2007/10/02)
The reaction of β-substituted organolithium derivatives with several electrophiles leads to mono- as well as bifunctionalized organic compounds.Thus, by treatment of these dianions with alkyl halides a direct attack on the carbanionic carbon atom is performed, giving as a result substituted amines.When dimethyl disulfide is used, β-amino and β-hydroxy thioethers are obtained.Finally, on reaction with imines, 1-amino-3-hydroxy compounds and 1,3-diamines are obtained.Since these dianions are easily preparated by mercury-lithium transmetalation from β-substituted organomercurials resulting from the addition of mercury(II) salts to olefins, this whole process gives an appropriate way of functionalizing olefins.
