52190-44-0Relevant academic research and scientific papers
Air Oxidative Radical Oxysulfurization of Alkynes Leading to α-Thioaldehydes
Zhou, Shao-Fang,Pan, Xiang-Qiang,Zhou, Zhi-Hao,Shoberu, Adedamola,Zhang, Pei-Zhi,Zou, Jian-Ping
, p. 5348 - 5354 (2015/05/27)
Air oxidative radical oxysulfurization of alkynes initiated by 0.5 mol % tert-butyl hydroperoxide with arylthiols is described. The reaction proceeded at room temperature in the presence of 5% mol water to afford selective α-thioaldehydes. (Chemical Equation Presented).
α-Organylchalcogenation of aldehydes and ketones with diorganyl dichalcogenides promoted by K3PO4
Movassagh, Barahman,Yousefi, Ali
, p. 1173 - 1177 (2014/06/24)
A new catalytic method for direct α-organylchalcogenation of aldehydes and ketones has been developed. When various aldehydes and ketones were allowed to react with diorganyl dichalcogenides in the presence of K 3PO4, under mild reac
ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS
-
Page/Page column 54-56; 106-108, (2010/02/15)
The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo--selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R", NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ("hydrocarbyl") group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R" are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R" form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R" are attached; and wherein said compound is free from a metal catalyst.
Direct, organocatalytic α-sulfenylation of aldehydes and ketones
Wang, Wei,Li, Hao,Wang, Jian,Liao, Lixin
, p. 8229 - 8231 (2007/10/03)
A method for direct sulfenylation of aldehydes and ketones, catalyzed by a novel pyrrolidine trifluoromethanesulfonamide organocatalyst, has been developed. This process serves as an efficient and mild approach to the preparation of α-phenylthio-ketones and -aldehydes.
Do the electronic effects of sulfur indeed control the π-selectivity of γ-sulfenyl enones? An investigation
Yadav, Veejendra K.,Babu, K. Ganesh,Parvez, Masood
, p. 3866 - 3874 (2007/10/03)
The electronic effects of sulfur in γ-sulfenyl enones are not transmitted to the carbonyl carbon through the π bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising
α-Sulfenylation of acylsilanes and aldehydes with N- (phenylthio)succinimide
Huang, Chih-Hao,Liao, Kang-Shyang,De, Surya Kanta,Tsai, Yeun-Min
, p. 3911 - 3914 (2007/10/03)
The reactions of acylsilanes with N-(phenylthio)succinimide in the presence of p-toluenesulfonic acid in acetonitrile give α-sulfenylated acylsilanes in good yields. Aldehydes with α-alkyl substituent afford moderate yields of α-sulfenylated products unde
CAN- and DDQ-Promoted Oxidation of Alkenyl Sulfides
Capella, Laura,Montevecchi, Pier Carlo,Nanni, Daniele
, p. 7379 - 7382 (2007/10/02)
Vinyl sulfides 1 react with CAN in acetonitrile at room temperature to give radical cations 2A in equilibrium with the thiiranyl radical cations 2B.The reaction products arise from nucleophilic attack of the nitrate counterion at either the sulfur atom of 2A or the trivalent carbon of 2B.The last reaction can proceed through 1,2-shift or displacement of the sulfide moiety.When α-methylenic protons are present in 2B, deprotonation occurs, leading to allyl radicals and, ultimately, to isomeric allyl alcohols.Reactions of 1 with DDQ in acetonitrile afford charge-transfer complexes and then zwitterionic electron-transfer (ET) complexes which can evolve rapidly through intramolecular proton transfer when trans methylenic protons are present.The resulting sulfur-oxygen ?-complexes are responcible for the reaction products mainly through either γ-elimination of DDQH2 or nucleophilic attack at the δ-vinilic carbon followed by displacement of DDQH(1-).
One electron transfer reaction of phenyl vinyl sulfides with dioxygen. The fate of the intermediate vinyl sulfide radical cations
Benati,Montevecchi,Nanni,Spagnolo
, p. 3595 - 3598 (2007/10/02)
Mild reaction of phenyl vinyl sulfides with dioxygen can lead to the eventual formation of rearranged vinyl sulfides and/or carbonyl-containing sulfide products, which are believed to result from decomposition of initially-formed vinyl sulfide radical cations. Supporting evidence is provided by the comparable findings obtained from the one electron oxidation of one vinyl sulfide by cerium (IV) ammonium nitrate.
