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

被引：6

作者：

Krylov, A. V. ^{[1
]}

Mokhammed, A. Kh ^{[1
]}

Yegorova, V. V. ^{[1
]}

Borisova, E. Ya ^{[1
]}

Borisova, N. Yu ^{[1
]}

Flid, V. R. ^{[1
]}

机构：

[1] MV Lomonosov Moscow State Univ Fine Chem Technol, Moscow 119571, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2012年 / 61卷 / 06期

关键词：

epoxides; ring opening; nucleophiles;

D O I：

10.1007/s11172-012-0153-z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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 alpha-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 E (T) and AN for neat solvents.

引用

页码：1128 / 1132

页数：5

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
A. V. Krylov
A. Kh. Mokhammed
V. V. Yegorova
E. Ya. Borisova
N. Yu. Borisova
V. R. Flid
Russian Chemical Bulletin, 2012, 61 : 1128 - 1132
[2] Enantiomerically pure 2-aryl(alkyl)-2-trifluoromethylaziridines: synthesis and ring opening with selected O- and N-nucleophiles
Grellepois, Fabienne
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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
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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

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