Solvent effect on regioselectivity of epoxide ring opening in styrene oxide by O- and N-nucleophiles in neutral and basic media

被引:0
|
作者
A. V. Krylov
A. Kh. Mokhammed
V. V. Yegorova
E. Ya. Borisova
N. Yu. Borisova
V. R. Flid
机构
[1] M. V. Lomonosov Moscow State University of Fine Chemical Technologies,
来源
Russian Chemical Bulletin | 2012年 / 61卷
关键词
epoxides; ring opening; nucleophiles;
D O I
暂无
中图分类号
学科分类号
摘要
The results of ring opening in styrene oxide by alcohols, amines, amino alcohols, and diamines were generalized. On low polarizing ability of the solvent, the main direction of the process is the formation of normal α-substituted products. The solvent effect on regioselectivity of the reaction was studied for N,N-diethylethylenediamine. The ratio of products correlates well with the value of dielectric constant for mixed aqueous-organic solvents and with the parameters of polarity ET and AN for neat solvents.
引用
收藏
页码:1128 / 1132
页数:4
相关论文
共 8 条
  • [1] Solvent effect on regioselectivity of epoxide ring opening in styrene oxide by O- and N-nucleophiles in neutral and basic media
    Krylov, A. V.
    Mokhammed, A. Kh
    Yegorova, V. V.
    Borisova, E. Ya
    Borisova, N. Yu
    Flid, V. R.
    RUSSIAN CHEMICAL BULLETIN, 2012, 61 (06) : 1128 - 1132
  • [2] Enantiomerically pure 2-aryl(alkyl)-2-trifluoromethylaziridines: synthesis and ring opening with selected O- and N-nucleophiles
    Grellepois, Fabienne
    Nonnenmacher, Jean
    Lachaud, Fabien
    Portella, Charles
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (04) : 1160 - 1168
  • [3] Highly Enantioselective Ring-Opening of meso-Epoxides with O- and N-Nucleophiles Catalyzed by a Chiral Sc(III)/bipyridine Complex
    Malatinec, Stefan
    Bednarova, Eva
    Tanaka, Hiroki
    Kotora, Martin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (08) : 1249 - 1257
  • [4] Ag(I)-Catalyzed Regioselective Ring-Opening of N-Tosylaziridine and N-Tosylazetidine with S-, O-, and N-Nucleophiles and Tethered Dinucleophiles
    Bera, Milan
    Pratihar, Sanjay
    Roy, Sujit
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05): : 1475 - 1478
  • [5] Regioselective ring opening of styrene oxide by carbon nucleophiles catalyzed by metal-organic frameworks under solvent-free conditions
    Anbu, Nagaraj
    Dhakshinamoorthy, Amarajothi
    JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2018, 58 : 9 - 17
  • [6] Solvent effect in the Cp2TiCl-catalyzed living radical polymerization of styrene initiated by epoxide radical ring opening
    Asandei, Alexandru D.
    Moran, Isaac W.
    Chen, Yanhui
    Saha, Gobinda
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [7] DIASTEREOSELECTIVE RING-OPENING OF ACHIRAL BRIDGED BIARYLS USING CHIRAL O-NUCLEOPHILES AND N-NUCLEOPHILES - 1ST ATROPO-ENANTIOSELECTIVE SYNTHESIS OF (-)-4,4'-BIS(ORCINOL)
    BRINGMANN, G
    WALTER, R
    EWERS, CLJ
    SYNLETT, 1991, (08) : 581 - 583
  • [8] DBU-assisted 1,3,2-oxathiaphospholane ring-opening condensation with selected O-, S-, N- and C-nucleophiles
    Misiura, K
    Szymanowicz, D
    Olesiak, M
    Stec, WJ
    TETRAHEDRON LETTERS, 2004, 45 (22) : 4301 - 4305