Synthesis of a new zwitterionic cyclopentadienyl-imidazolium compound and isolation of the 3,3′-(trans-3,5-cyclopentenyl)-di(1-tert-butylimidazolium)bromide intermediate

被引：9

作者：

Coleman, KS

Turberville, S

Pascu, SI

Green, MLH

机构：

[1] Univ Durham, Dept Chem, Durham DH1 3LE, England

[2] Univ Oxford, Inorgan Chem Lab, Oxford OX1 3QR, England

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 47期

基金：

英国工程与自然科学研究理事会;

关键词：

zwitterion; N-heterocyclic carbene; imidazolium; cyclopentadienyl;

D O I：

10.1016/j.tetlet.2004.09.137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The new zwitterionic compound 1-tert-butylimidazolium-cyclopentadienylide, shown to have a polar ground state and a non-polar fulvene-like excited state, has been synthesised and the intermediate 3,3'-(trans-3,5-cyclopentenyl)di(1-tert-butylimidazolium)bromide isolated and structurally characterised. (C) 2004 Elsevier Ltd. All rights reserved.

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收藏

页码：8695 / 8698

页数：4

相关论文

共 14 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[3] Silver(I) complex of a new imino-N-heterocyclic carbene and ligand transfer to palladium(II) and rhodium(I) [J].

Coleman, KS ;

Chamberlayne, HT ;

Turberville, S ;

Green, MLH ;

Cowley, AR .

DALTON TRANSACTIONS, 2003, (14) :2917-2922

[4] HYDROGEN-BONDING IN IMIDAZOLIUM SALTS AND ITS IMPLICATIONS FOR AMBIENT-TEMPERATURE HALOGENOALUMINATE(III) IONIC LIQUIDS [J].

ELAIWI, A ;

HITCHCOCK, PB ;

SEDDON, KR ;

SRINIVASAN, N ;

TAN, YM ;

WELTON, T ;

ZORA, JA .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1995, (21) :3467-3472

[5]

Frisch M.J., 1998, GAUSSIAN 98

[6]

Fuchs B, 1978, TOP STEREOCHEM, V10, P1

[7] THE ION RADICAL SALT OF 1-METHYL-3-PROPYLIMIDAZOLIUM WITH 7,7,8,8-TETRACYANO-PARA-QUINODIMETHANE - MPI+.TCNQ- [J].

LANGER, V ;

HUML, K ;

RECK, G .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 1982, 38 (JAN) :298-300

[8]

LLOYD D, 1955, CHEM IND-LONDON, P1220

[9] Processing of X-ray diffraction data collected in oscillation mode [J].

Otwinowski, Z ;

Minor, W .

MACROMOLECULAR CRYSTALLOGRAPHY, PT A, 1997, 276 :307-326

[10] TRIPHENYLPHOSPHONIUMCYCLOPENTADIENYLIDE [J].

RAMIREZ, F ;

LEVY, S .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :488-489