ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES

被引：1091

作者：

ARDUENGO, AJ

DIAS, HVR

HARLOW, RL

KLINE, M

机构：

[1] Du Pont Central Research, Experimental Station, Wilmington

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1992年 / 114卷 / 14期

关键词：

D O I：

10.1021/ja00040a007

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Four new stable nucleophilic carbenes have been synthesized and structurally characterized. The remarkable ability of the imidazole nucleus to stabilize a carbene center at the C-2 position is demonstrated by the isolation of 1,3,4,5-tetramethylimidazol-2-ylidene. The isolation of three imidazol-2-ylidenes that bear aryl substituents is counter to speculations based on previous reports.

引用

页码：5530 / 5534

页数：5

共 22 条

[1] UPON THE STRUCTURE OF ROOM-TEMPERATURE HALOGENOALUMINATE IONIC LIQUIDS
ABDULSADA, AK
GREENWAY, AM
HITCHCOCK, PB
MOHAMMED, TJ
SEDDON, KR
ZORA, JA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (24) : 1753 - 1754
[2] [Anonymous], 1991, US Patent, Patent No. [5077414, 5,077,414]
[3] A STABLE CRYSTALLINE CARBENE
ARDUENGO, AJ
HARLOW, RL
KLINE, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) : 361 - 363
[4] SYNTHESIS OF A REVERSE YLIDE FROM A NUCLEOPHILIC CARBENE
ARDUENGO, AJ
KLINE, M
CALABRESE, JC
DAVIDSON, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) : 9704 - 9705
[5] ACIDITIES OF C2 HYDROGEN-ATOMS IN THIAZOLIUM CATIONS AND REACTIVITIES OF THEIR CONJUGATE BASES
BORDWELL, FG
SATISH, AV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) : 985 - 990
[6] ELECTRONIC-STRUCTURE OF LAMBDA-5-PHOSPHAACETYLENES AND CORRESPONDING TRIPLET METHYLENES
DIXON, DA
DOBBS, KD
ARDUENGO, AJ
BERTRAND, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) : 8782 - 8785
[7] ELECTRONIC-STRUCTURE OF A STABLE NUCLEOPHILIC CARBENE
DIXON, DA
ARDUENGO, AJ
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (11) : 4180 - 4182
[8] DOERING WVE, 1956, J AM CHEM SOC, V78, P4947
[9] [BIS(DIISOPROPYLAMINO)PHOSPHINO]TRIMETHYLSILYLCARBENE - A STABLE NUCLEOPHILIC CARBENE
IGAU, A
BACEIREDO, A
TRINQUIER, G
BERTRAND, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (05): : 621 - 622
[10] ANALOGOUS ALPHA,ALPHA'-BIS-CARBENOID TRIPLY BONDED SPECIES - SYNTHESIS OF A STABLE LAMBDA-3-PHOSPHINOCARBENE LAMBDA-5-PHOSPHAACETYLENE
IGAU, A
GRUTZMACHER, H
BACEIREDO, A
BERTRAND, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (19) : 6463 - 6466

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