19149-98-5Relevant academic research and scientific papers
Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction
Carlet, Federica,Bertarini, Greta,Broggini, Gianluigi,Pradal, Alexandre,Poli, Giovanni
supporting information, p. 2162 - 2168 (2021/04/02)
A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.
Synthesis of quaternary carbon centers via hydroformylation
Sun,Frimpong,Tan
supporting information; experimental part, p. 11841 - 11843 (2010/11/04)
The application of hydroformylation to the synthesis of quaternary carbon centers is reported. The synthesis of the highly substituted carbon is achieved by applying a catalytic amount of 1. Ligand 1 serves as a catalytic directing group by covalently and reversibly binding to both the substrate and catalyst. The intramolecular nature of the directing group strategy accelerates the hydroformylation reaction such that the reaction is performed at mild temperatures (35-55 °C) and with excellent regioselectivity (b:l > 94:6).
Regio- and stereoselective hydrostannation of allenes using dibutyliodotin hydride (Bu2SnIH) and successive coupling with aromatic halides
Hayashi, Naoki,Kusano, Kazunao,Sekizawa, Shingo,Shibata, Ikuya,Yasuda, Makoto,Baba, Akio
, p. 4913 - 4915 (2008/09/18)
Regio- and stereoselective hydrostannation of allenes by using di-n-butyliodotin hydride (Bu2SnIH) was accomplished to give α,β-disubstituted vinyltins, which induced the synthesis of multi-substituted alkenes in a one-pot procedure. The Royal Society of Chemistry.
γ-1,4 Addition of substituted methoxyallylcopper reagents to methylvinylketone
Berrien, Jean-Francois,Raymond, Marie-Noelle,Zaari, Fatima,Moskowitz, Henri,Mayrargue, Joelle
, p. 3367 - 3370 (2007/10/03)
Methoxyallylcopper reagents substituted in α and/or β position of methoxy group reacted regiospecifically with MVK to give γ-1,4 adducts, i.e. ketoenolethers, γ substituted methoxyallylcopper reagents gave mixtures of γ-1,4 and α-1,4 adducts.
Flash Vacuum Thermolysis of Phenylcyclopropanecarbaldoximes and Its Methyl Ethers
Wu, Pei-Lin,Wang, Wen-Shan,Chen, Chang-Fu
, p. 601 - 604 (2007/10/03)
Flash vacuum thermolysis of 1-phenylcyclopropane-1-carbaldoxime at 500 deg C produced mainly 3-phenylpyrrole.The products after thermolysis of its oxime methyl ether were α-methoxymethylstyrene, α-methylstyrene, and a dimer 2,5-diphenyl-1,5-hexadiene. - Key Words Flash vacuum thermolysis; 3-Phenylpyrrole; Phenylcyclopropanecarbaldoxime; Phenylcyclopropanecarbaldoxime methyl ether.
Deamination Reactions, 45. Decomposition of 1-Arylcyclopropanediazonium Ions
Kirmse, Wolfgang,Rode, Jutta
, p. 3694 - 3703 (2007/10/02)
1-Arylcyclopropanediazonium ions have been generated by alkaline cleavage of the analogous nitrosocarbamates in methanol.With increasing ?-donor capacity of the aryl groups, retention of the three-membered ring was enhanced while the stereoselectivity (as probed with the aid of 2-D labels) was diminished or entirely lost (4-methoxyphenyl).Where applicable, the stereoselectivity of ring opening is inferior to that of nucleophilic displacement.The data may be interpreted in terms of competing reactions (ks, kc, kΔ) of the cyclopropanediazonium ions.
Reaction of Diazonium Salts with Transition Metals. Part 11. Palladium-catalyzed Aryldesilylation of Alkenylsilanes by Arenediazonium Salts
Ikenaga, Kazutoshi,Kikukawa, Kiyoshi,Matsuda, Tsutomu
, p. 1959 - 1964 (2007/10/02)
Under palladium(0) catalysis, both (E)- and (Z)-RCH=CHSiMe3(R=Rh, 4-MeC6H4, 4-NO2C6H4, n-C6H13, and MeOCH2) were easily aryldesilylated by ArN2X(Ar=Ph, 4-MeC6H4, 4-BrC6H4 and 4-NO2C6H4; X=BF4, PF6, and Cl) to give (E)-RCH=CHAr and RC(Ar)=CH2 as the main products at 25 deg C in acetonitrile. anti- and syn-1,2-Elimination of Pd(0) and Me3Si from the adducts, threo- and erythro-RCH(PdX)CHSiMe3, generated from ArPdX and (E) and (Z)-RCH=CHSiMe3, respectively, are proposed for the formation of (E)-RCH=CHAr from either isomer of RCH=CHSiMe3.
Photochemical Electron-transfer Reactions of Biphenyl-2,2'-dicarboximide and Naphthalene-1,8-dicarboximide with Olefin. Dependence of the Reaction Course on the Structure of the Aromatic Imide
Kubo, Yasuo,Araki, Takeo,Maruyama, Kazuhiro
, p. 2863 - 2869 (2007/10/02)
Photoreactions of N-methylbiphenyl-2,2'-dicarboximide and N-ethylnaphthalene-1,8-dicarboximide (2) with 1,1-diphenylethylene (3) in methanol gave methanol-incorporated 1:1:1-adduct (7) and 2,2-diphenylethyl methyl ether (6), an anti-Markovnikov adduct of methanol to 3.The ratio of the two types of products largely depends on the structure of the aromatic imides.Probably the spin densities of the radical anions of the aromatic imides seem to play an important role to determine the reaction courses after the photochemical electron-transfer process.Similar results were obtained in the photoreaction of N-(2-phenylallyl)aromatic imides; elimination induced by methanol-incorporation vs. anti-Markovnikov addition of methanol. Photoreactions of N-(trans-3-phenylallyl) aromatic imides in methanol gave methanol-incorporated O-cyclized products (20 and 27) and C-cyclized products (21 and 28).A tentative mechanism for the O-cyclization is proposed; i.e., intramolecular electron transfer followed by anti-Markovnikov addition of methanol to the radical cation of the double bond moiety, nucleophilic attack of the aromatic imide radical anion moiety, secondary electron-transfer, and then polar addition of methanol.
STEREOSPECIFIC PHENYLATION OF ALKENYLSILANES WITH PHENYLPALLADIUM ACETATE
Kikukawa, Kiyoshi,Ikenaga, Kazutoshi,Wada, Fumio,Matsuda, Tsutomu
, p. 5789 - 5792 (2007/10/02)
(E)- and (Z)-RCH=CHSiMe3 (R= Ph, n-C6H13, CH3OCH2) reacted stereospecifically with Ph-Pd-OAc to give RCH=C(Ph)SiMe3 and R(Ph)C=CHSiMe3 with inversion of the starting geometry with respect to R and Me3Si groups.
PHOTO-INDUCED HIGHLY SELECTIVE OLEFIN-MIGRATION OF N-(2- OR 3-PHENYLALLYL) AROMATIC IMIDES
Kubo, Yasuo,Araki, Takeo,Maruyama, Kazuhiro
, p. 1909 - 1912 (2007/10/02)
A highly selective migration of double bond was observed on irradiation of N-(2- or 3-phenylallyl) aromatic imides in acetonitrile to afford N-(2- or 3-phenyl-1-propenyl) aromatic imides.The reaction seems to proceed via photochemical intramolecular one electron transfer from the double bond to the imide moiety.
