A stepwise, zwitterionic mechanism for the 1,3-dipolar cycloaddition between (Z)-C-4-methoxyphenyl-N-phenylnitrone and gem-chloronitroethene catalysed by 1-butyl-3-methylimidazolium ionic liquid cations

被引：113

作者：

Jasinski, Radomir ^{[1
]}

机构：

[1] Cracow Univ Technol, Inst Organ Chem & Technol, PL-31155 Krakow, Poland

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 03期

关键词：

1,3-Dipolar cycloaddition; Stepwise mechanism; Nitroalkene; Nitrone; Ionic liquids; DFT; YLIDES; STEREOSELECTIVITY;

D O I：

10.1016/j.tetlet.2014.12.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DFT calculations at different levels of theory indicate consistently that in the presence of 1-butyl-3-methylimidazolium cations, a 1,3-dipolar cycloaddition between gem-chloronitroethene and (Z)-C-4-methoxyphenyl-N-phenylnitrone is expected to take place much faster than under 'conventional' conditions, the one-step mechanism being replaced by a two-step mechanism involving a zwitterionic intermediate. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：532 / 535

页数：4

共 26 条

[1] Use of Ionic Liquids for the Diels-Alder Reaction of Oleochemicals [J].

Behr, A. ;

Naendrup, F. ;

Nave, S. .

ENGINEERING IN LIFE SCIENCES, 2003, 3 (08) :325-327

[2] Synthesis of 5-aminoisoxazolines from N-allyl compounds and nitrile oxides via tandem isomerization-1,3-dipolar cycloaddition [J].

Bujak, Piotr ;

Krompiec, Stanislaw ;

Malarz, Joanna ;

Krompiec, Michal ;

Filapek, Michal ;

Danikiewicz, Witold ;

Kania, Magdalena ;

Gebarowska, Katarzyna ;

Grudzka, Iwona .

TETRAHEDRON, 2010, 66 (32) :5972-5981

[3] Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model [J].

Cossi, M ;

Rega, N ;

Scalmani, G ;

Barone, V .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 2003, 24 (06) :669-681

[4] Understanding the origin of the asynchronicity in bond-formation in polar cycloaddition reactions. A DFT study of the 1,3-dipolar cycloaddition reaction of carbonyl ylides with 1,2-benzoquinones [J].

Domingo, L. R. ;

Aurell, M. J. ;

Perez, P. ;

Saez, J. A. .

RSC ADVANCES, 2012, 2 (04) :1334-1342

[5] A DFT study of the Huisgen 1,3-dipolar cycloaddition between hindered thiocarbonyl ylides and tetracyanoethylene [J].

Domingo, LR ;

Picher, MT .

TETRAHEDRON, 2004, 60 (23) :5053-5058

[6]

Domingo LR, 2000, EUR J ORG CHEM, V2000, P2265

[7] Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions.: A theoretical study [J].

Domingo, Luis R. ;

Chamorro, Eduardo ;

Perez, Patricia .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4615-4624

[8] Understanding the mechanism of polar Diels-Alder reactions [J].

Domingo, Luis R. ;

Saez, Jose A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (17) :3576-3583

[9] Understanding the role of the Lewis acid catalyst on the 1,3-dipolar cycloaddition of N-benzylideneaniline N-oxide with acrolein:: a DFT study [J].

Domingo, Luis Ramon ;

Benchouk, Wafaa ;

Mekelleche, Sidi Mohamed .

TETRAHEDRON, 2007, 63 (21) :4464-4471

[10]

Frisch M. J., 2016, GAUSSIAN 16

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