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An Estimation of the $\pi$-Bond Energy of 1-Methyl-1-Phenyl-2-Neopentylsilene
Lee Myong Euy,Paul R. Jones Korean Chemical Society 1994 Bulletin of the Korean Chemical Society Vol.15 No.6
The E-and Z-isomers of 1-methyl-l-phenyl-2-neopentylsilene, generated by the sealed tube thermolyses of their anthracene adducts are stereospecifically trapped by trimethylmethoxysilane to give diastereomeric adducts. The temperature dependence of the ratio of the two diastereomers obtained when the silene formed from the pure E-or Z-anthracene adduct was trapped at higher temperatures permitted the determination of an activation energy for the silene isomerization. The activation energies for the E-to Z-and Z-to E-silene isomerization are $45{\pm}$6 and $20{\pm}4$ kcal $mol^{-1}$, respectively. The significance of these values is discussed.
Acid-Promoted Ring Cleavage Reactions of Silacyclohex-3-ene Derivatives
Myong Euy Lee,Jeong Hyun Kim,Chang Hwan Kim Korean Chemical Society 1994 Bulletin of the Korean Chemical Society Vol.15 No.9
The acid-promoted cleavage of the E-and Z-isomers of 1-phenyl-6-neopentyl-1,3,4-trimethyl-1-silacyclohe x-3-ene(II) under various conditions gave clean and nearly quantitative formation of the ring-opened 2,3,7,7-tetramethyl-5-(X)silyl-1-octene products (X=OMe, Cl, OH). The possible mechanism for the formation of the ring-opened products was suggested that the initial protonation of II at C-4 would give a carbocation oriented so that they are ${\beta}$ to the silicon atom, and the subsequent nucleophilic attack at silicon would give rise to the observed products (VI, VII, VIII).
金長煥,李鳴儀 연세대학교 대학원 1977 延世論叢 Vol.14 No.2
In order to see the effect of d-orbitals of silicon on the ring π-electrons of ferrocene, the trice- thylsilyl derivatives of ferrocene were prepared. The reaction of 1,1'-bis (trimethylsilyl) ferrocene with mercery (II) chloride gave 1'-trimetalylsilylferrocenylmercury (II) chloride, which was converted to 1-carboxy-1'- (trimethylsilyl) ferrocene through lithiation followed by carbonation reaction. By the potentiometric titration, the pKa values of ferrocenecarboxylic acid and 1-carboxy-1'- (trimethylsilyl) ferrocene were found to be 6.11 and 5.98 respectively at 25℃ and were compared with the literature values of other alkylated ferrocenecarboxylic acids. Contrary to the expectation by the inductive effect of trimethylsilyl group, 1-carboxy-1'- (trimethylsilyl) ferrocene was found to be slightly stronger acid than ferrocenoic acid. This can be explained only by assuming that the 3d-orbital of silicon overlap extensively With the ring π-orbital find form dπ-pπ dative bond. This dπ-dπ bonding appears to be an important factor, enough to compensate the inductive effect, in stabilizing the conjugate base form of the trimethylsilyl substituted ferrocenoic acid by withdrawing the electronic charge away from the cyclorentadienyl ring system.
Gong, Seong-Deok,Lee, Chang-Yeob,Yoo, Bok-Ryul,Lee, Myong-Euy,Jung, Il-Nam Korean Chemical Society 2002 Bulletin of the Korean Chemical Society Vol.23 No.9
Friedel-Crafts alkylation reaction of an isomeric mixture of 1,2,3,4,5,6,7,8- (2) and 1,2,3,4,5,6,7,8-octahydrophenanthrene (2') with excess vinylchlorosilanes such as vinyl(methyl)dichlorosilane (1a) and vinyltrichlorosilane (1b) in the presence of aluminum chloride catalyst at 80 $^{\circ}C$ gives only one dialkylated products, 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthrenes [(Cl2XSiCH2CH2)2C14H16: X = Me (4a), Cl (4b)] in good yields, but 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydrophenanthrenes are not obtained. However, monoalkylation of 2 with 1 affords a mixture of both isomeric compounds, 9-[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthracenes 3 and -phenanthrenes 3'. The yield of product 3' is always higher than that of 3. When a mixture of 3 and 3' is alkylated again with 1, only product 4 without phenanthrene type compounds is obtained, indicating that the isomerizations between 2 and 2', or 3 and 3'occur under the alkylation condition. The alkylation with dimethylvinylchlorosilane or trimethylvinylsilane did not proceed. The structure of 4a is determined by X-ray single crystal diffraction analysis.
Jung, Hyo-Jin,Lee, Myong-Euy,Lim, Chae-Yun,Paeng, Ki-Jung Korean Chemical Society 2005 Bulletin of the Korean Chemical Society Vol.26 No.1
The potentiometric responses for various anions are investigated with membrane electrode (membrane 1) based on 1,3-diethyl-1,3-dihydroxy-1,3-bis(2-dimethylaminomethyl ferrocenyl) disiloxane. The nitrate ion-selective electrode based on compound 1 gave a good Nernstian response of 58.18 mV per decade for nitrate with the detection limit of −e5.66 of log [NO3−e]. Compound 1 has all those functional groups and the other two compounds have less functional group of ferrocenyl or ferrocenyl and hydroxide, respectively. Even though, potentiometric response to anions was excellent at pH 5, the selectivity pattern for all three membrane electrode based on series of disiloxane is almost like Hofmeister sequence at pH 5. However, the membrane electrode 1-3 exhibited very different response to anions at pH 7. In this pH, NH2 is not protonated and ionophore may act as neutral carrier. Hydrogen bond may enhance the responsibility to hydrogen acceptors and intramolecular electro-active site may increase the permeability of analyte to ionophore in membrane.
Reactivities of chlorotrisylsilylenoid with ketones
Cho, Hyeon Mo,Lim, Young Mook,Lee, Myong Euy Royal Society of Chemistry 2010 Dalton Transactions Vol.39 No.39
<P>Chlorotrisylsilylenoid 1 reacted with both acetophenone and benzil to give the corresponding 2,5-dioxasilolanes and silylethers, respectively.</P> <P>Graphic Abstract</P><P>The reactions of a stable chlorotrisylsilylenoid with acetophenone and benzil were carried out to afford 2,5-dioxasilolane and silylether compounds. This result will provide a new synthetic route for functional silaheterocycles. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c0dt00147c'> </P>
Kim, Cheol Hyun,Cho, Hyeon Mo,Lee, Myong Euy Korean Chemical Society 2014 Bulletin of the Korean Chemical Society Vol.35 No.6
Four multialkoxy-functionalized siloxane base-polymers (BP-1~4) were synthesized through either hydrosilylation or condensation reactions in order to prepare multi-networked siloxane polymers having appropriate physical properties for protective coating in fabrications of electronics. Formulations of 4 base-polymers gave coating materials A and B. Product A showed well-controlled flowing and leveling properties, and product A-2 was successfully applied to protective insulating coating for junction areas of connectors and chips in PDP controller. Tack free time, extrusion rate, dielectric breakdown voltage, hardness, thermal stability, water resistance and flame resistance of products A and B were examined.