ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES

被引:1094
作者
ARDUENGO, AJ
DIAS, HVR
HARLOW, RL
KLINE, M
机构
[1] Du Pont Central Research, Experimental Station, Wilmington
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
收藏
页码:5530 / 5534
页数:5
相关论文
共 22 条
[1]   UPON THE STRUCTURE OF ROOM-TEMPERATURE HALOGENOALUMINATE IONIC LIQUIDS [J].
ABDULSADA, AK ;
GREENWAY, AM ;
HITCHCOCK, PB ;
MOHAMMED, TJ ;
SEDDON, KR ;
ZORA, JA .
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 [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[4]   SYNTHESIS OF A REVERSE YLIDE FROM A NUCLEOPHILIC CARBENE [J].
ARDUENGO, AJ ;
KLINE, M ;
CALABRESE, JC ;
DAVIDSON, F .
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 [J].
BORDWELL, FG ;
SATISH, AV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :985-990
[6]   ELECTRONIC-STRUCTURE OF LAMBDA-5-PHOSPHAACETYLENES AND CORRESPONDING TRIPLET METHYLENES [J].
DIXON, DA ;
DOBBS, KD ;
ARDUENGO, AJ ;
BERTRAND, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8782-8785
[7]   ELECTRONIC-STRUCTURE OF A STABLE NUCLEOPHILIC CARBENE [J].
DIXON, DA ;
ARDUENGO, AJ .
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 [J].
IGAU, A ;
BACEIREDO, A ;
TRINQUIER, G ;
BERTRAND, G .
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 [J].
IGAU, A ;
GRUTZMACHER, H ;
BACEIREDO, A ;
BERTRAND, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (19) :6463-6466