• 제목/요약/키워드: nucleophilic substitution

검색결과 275건 처리시간 0.021초

Ionic Liquids: An Environmentally Friendly Media for Nucleophilic Substitution Reactions

  • Jorapur, Yogesh R.;Chi, Dae-Yoon
    • Bulletin of the Korean Chemical Society
    • /
    • 제27권3호
    • /
    • pp.345-354
    • /
    • 2006
  • Ionic liquids are alternative reaction media of increasing interest and are regarded as an eco-friendly alternatives, of potential use in place of the volatile organic solvents typically used in current chemical processing methods. They are emerging as the smart and excellent solvents, which are made of positive and negative ions that they are liquids near room temperature. The nucleophilic substitution reaction is one of the important method for inserting functional groups into a carbon skeleton. Many nucleophilic substitution reactions have been found with enhanced reactivity and selectivity in ionic liquid. In this review, some recent interesting results of nucleophilic substitution reactions such as hydroxylations, ether cleavages, carbon-X (X= carbon, oxygen, nitrogen, fluorine) bond forming reactions, and ring opening of epoxides in ionic liquids are discussed.

Dynamic Kinetic Resolution of α-Bromo Carboxylic Acid Derivatives in Asymmetric Nucleophilic Substitution with Chiral α-Amino Esters

  • Chang, Ji-Yeon;Shin, Eun-Kyoung;Kim, Hyun-Jung;Kim, Yong-Tae;Park, Yong-Sun
    • Bulletin of the Korean Chemical Society
    • /
    • 제26권6호
    • /
    • pp.989-992
    • /
    • 2005
  • Dynamic kinetic resolution of $\alpha$-bromo carboxylic acid derivatives in nucleophilic substitution with chiral $\alpha$-amino ester nucleophiles in the presence of TBAI and DIEA has been investigated for stereoselective syntheses of 1,1'-iminodicarboxylic acid derivatives. Nucleophilic substitutions with various chiral $\alpha$-amino esters gave iminodiacetates 2-8 with stereoselectivities up to 87 : 13 dr. Also, the reactions of N-($\alpha$-bromo-$\alpha$-phenylacetyl)-L-alanine methyl ester with L-alanine, D-alanine and glycine methyl ester nucleophiles afforded N-carboxyalkyl dipeptide analogues 10-12 up to 90 : 10 dr.

Determination of Nucleophilic Addition Constant to ${\beta}$-Nitrostyrene (I) (${\beta}$-Nitrostyrene에 대한 Nucleophilic Addition Constant의 측정 (I))

  • Kim, Tae-Rin;Choi, Young-Sang
    • Journal of the Korean Chemical Society
    • /
    • 제10권4호
    • /
    • pp.158-160
    • /
    • 1966
  • The nucleophilic addition constants 3,4-methylenedioxy-${\beta}$-nitrostyrene were determined for various nucleophiles. Considerably more data would be desirable, but it appears at present that there is no proportionality between the nucleophilic addition and substitution constant.

  • PDF

Highly Stable Photoluminescent Qunatum Dot Multilayers by Layer-by-Layer Assembly via Nucleophilic Substitution Reaction in Organic Media

  • Yun, Mi-Seon;Kim, Yeong-Hun;Jeong, Sang-Hyeok;Baek, Hyeon-Hui;Jo, Jin-Han
    • Proceedings of the Materials Research Society of Korea Conference
    • /
    • 한국재료학회 2011년도 춘계학술발표대회
    • /
    • pp.244.2-244.2
    • /
    • 2011
  • We introduce a novel and robust method for the preparation of nanocomposite multilayers, which allows the excellent photoluminescent (PL) properties as well as the accurate control over the composition and dimensions of multilayers. By exchanging the oleic acid stabilizers of CdSe@ZnS quantum dots (QDs) synthesized in organic solvent with 2-bromo-2-methylpropionic acid (BMPA) in the same solvent, these nanoparticles were be alternately deposited by nucleophilic substitution reaction with highly branched poly(amidoamine) dendrimer (PAMA) through layer-by-layer (LbL) assembly process. Our approach does not need to be transformed into the water-dispersible nanoparticles with electrostatic or hydrogen-bonding groups, which can deteriorate their inherent properties, for the built-up of multilayers. The nanocomposite multilayers including QDs exhibited the strong PL properties achieving densely packed surface coverage as well as long-term PL stability under atmospheric conditions in comparison with those of conventional LbL multilayers based on electrostatic interaction. Furthermore, we demonstrate that the flexible multilayer films with optical properties can be easily prepared using nucleophilic substitution reaction between bromo and amino groups in organic media. This robust and tailored method opens a new route for the design of functional film devices based on nanocomposite multilayers.

  • PDF

Dynamic Resolution of α-Bromo Tertiary Amides for Stereoselective Preparation of Dipeptide Analogues

  • Kim, Hyun-Jung;Chang, Ji-Yeon;Shin, Eun-Kyoung;Park, Yong-Sun
    • Bulletin of the Korean Chemical Society
    • /
    • 제26권2호
    • /
    • pp.273-277
    • /
    • 2005
  • Dynamic resolution of $\alpha$-bromo tertiary acetamides in asymmetric nucleophilic substitution reaction is described. Intermolecular substitution of $\alpha$-bromo tertiary acetamides with dibenzylamine in the presence of TBAI and $Et_3N$ gave the dipeptide analogues 7-10 with high stereoselectivities up to 90 : 10 dr. Also, cyclic dipeptide analogues 20-29 were produced by the intramolecular nucleophilic cyclization of $\alpha$-bromo tertiary acetamides with low stereoselectivities in 84-42% yields.