10152-76-8Relevant academic research and scientific papers
EFFICIENT AND/OR SELECTIVE METHYLATION BY DIAZOMETHANE OF ALCOHOLS, HALO ALCOHOLS, GLYCOLS, AMINO ALCOHOLS AND MERCAPTO ALCOHOLS WITH THE USE OF A PROTON-EXCHANGED X-TYPE ZEOLITE AS AN ACID-BASE BIFUNCTIONAL CATALYST
Takeuchi, Hiroshi,Kishioka, Hiroaki,Kitajima, Kunio
, p. 121 - 126 (1995)
Reactions of diazomethane with butanol, allyl alcohol and β- and γ-halo alcohols led to efficient methylation (giving the corresponding methyl ethers) with the use of a proton-excahnged X-type zeolite compared with H2SO4.The reactions with propylene and isobutylene glycols using the zeolite provided regioselective methylation of the primary OH rather than the secondary or tertiary OH, whereas regioselectivity was not observed in the reactions using H2SO4.The reactions with 2-aminoethanol and 2-mercaptoethanol showed high chemoselective S-methylation and N-monomethylation, respectively, in the presence of the zeolite instead of H2SO4.The mechanism for the reactions is proposed to involve acid-base bifunctional catalysis of the zeolite in which the acidic site reacts with diazomethane to form its conjugate acid, and the nucleophilicity of OH and SH groups is enhanced by the interaction of the basic site with the proton of the groups.
Matrix isolation and spectroscopic properties of the methylsulfinyl radical CH3(O)S
Reisenauer, Hans Peter,Romanski, Jaroslaw,Mloston, Grzegorz,Schreiner, Peter R.
, p. 9467 - 9469 (2013)
The atmospherically highly relevant methylsulfinyl radical CH 3(O)S was generated thermally under flash pyrolysis conditions and isolated in Ar matrices at 10 K; the allyl radical is a byproduct. CH 3(O)S and its D3- and 13C-isotopologues were characterized through the excellent agreement between experimental and computed IR and UV/Vis spectra.
Yb(iii)-catalysedsyn-thioallylation of ynamides
Dutta, Shubham,Gandon, Vincent,Gogoi, Manash Protim,Mallick, Rajendra K.,Prabagar, B.,Sahoo, Akhila K.,Vanjari, Rajeshwer,Yang, Shengwen
supporting information, p. 7521 - 7524 (2021/08/05)
Reported herein is asyn-thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium(iii)-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamidesyn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism.
Aqueous hemin catalyzed sulfonium ylide formation and subsequent [2,3]-sigmatropic rearrangements
Xu, Xiaofei,Li, Chang,Tao, Zhihao,Pan, Yuanjiang
supporting information, p. 1245 - 1249 (2017/08/15)
A mild hemin catalytic system for sulfonium ylide generation via a metal carbenoid and a subsequent [2,3]-sigmatropic rearrangement reaction in aqueous solvent is well-established, with the assistance of cyclodextrin (CD) and Triton X-100. The protocol displays high catalytic activity with a broad substrate scope of aryl/alkyl allyl sulfides and diazo reagents, affording homoallyl sulfide products in up to 99% yield. Notably, this catalytic system is successful for water-insoluble allyl sulfides but ineffective for allyl amines or allyl ethers. Moreover, an unprecedented cascade reaction of sulfonium ylide formation, [2,3]-sigmatropic rearrangement and C-H insertion was reported.
Using CS2 to Probe the Mechanistic Details of Decarboxylation of Bis(phosphinite)-Ligated Nickel Pincer Formate Complexes
Ma, Qiang-Qiang,Liu, Ting,Adhikary, Anubendu,Zhang, Jie,Krause, Jeanette A.,Guan, Hairong
, p. 4077 - 4082 (2017/01/10)
The reaction of the formate complex {2,6-(R2PO)2C6H3}Ni(OCHO) (R = tBu, 5; R = iPr, 6) with CS2 shows first-order kinetics in nickel concentration and zero-order in [CS2/su
Reactions of 2-(α-Haloalkyl)thiiranes with nucleophilic reagents: V.* Reactions of 2-(α-chloroalkyl)thiiranes with organolithium compounds
Tomashevskii,Sokolov,Potekhin
experimental part, p. 1822 - 1825 (2011/04/17)
2-(α-Haloalkyl)thiiranes reacted with methyl-, butyl-, and phenyllithium to give the corresponding allyl sulfides. The reactions of diastereoisomeric erythro-and threo-2-(1-chloroethyl)thiiranes with phenyllithium were stereospecific, and they afforded (E)-and (Z)-1-phenylsulfanylbut-2-enes, respectively. 3-Chloromethyl-2,2- dimethylthiirane and phenyllithium gave rise to a mixture of 3-methyl-3-phenylsulfanylbut-1-ene and 3-methyl-1-phenylsulfanylbut-2-ene. The reactions of 2-chloromethylthiiranes with phenyllithium and methyllithium in the presence of a catalytic amount of copper(I) iodide (10 mol %) led to the formation of substituted thiiranes as the major products. Mechanisms of the observed transformations are discussed. Pleiades Publishing, Ltd., 2010.
INTEGRIN MODULATORS AND METHODS FOR THEIR USE
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Page/Page column 56, (2008/06/13)
1,5-Dithiaocta-2,7-diene-5-oxide-1-yl(DODOyl) compounds and derivatives thereof, referred to collectively as DODOyl-derived compounds (DDCs), and chiral enantiomers and derivatives thereof, are described, which are integrin modulators that modulate integrin-mediated functions and/or processes. Pharmaceutical compositions containing integrin modulators and chiral enantiomers thereof, and methods for using integrin modulators and chiral enantiomers thereof are further described.
Antiviral composition derived from allium CEPA and therapeutic use thereof
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, (2008/06/13)
Novel medicinal extracts derived from Allium species, preferablyAllium cepaare provided. These extracts have broad medicinal properties, especially for treatment of AIDS and other viral infections.
Isomerization processes in the synthesis of asymmetric allyl chalcogenides
Deryagina,Korchevin
, p. 223 - 225 (2007/10/03)
Allyl-propenyl rearrangement (prototropic isomerization) occurs in the synthesis of allyl organyl chalcogenides in a hydrazine hydrate - KOH system with a 6 - 10-fold molar excess of KOH. Specificities of the rearrangement that depend on the nature of the chalcogen were studied.
Structure-Stability Relationships in Vinyl Sulfides. III. Stabilization Caused by Different Alkylthio and Phenylthio Groups Attached to an Olefinic Double Bond
Kimmelma, Reijo
, p. 550 - 555 (2007/10/02)
The stabilization energies of different alkylthio and phenylthio groups attached to an olefinic double bond have been evaluated with respect to the energy differences of the isomerization reactions of some unsaturated sulfides, in which the double bond migrates from the β,γ- to the α,β-position.According to these results the stabilization energies (in kJ mol-1) are: MeS 15.6, EtS 14.8, i-PrS 15.7, t-BuS 17.5 and PhS 14.4
