An aromatic-antiaromatic switch in P-heteroles.: A small change in delocalisation makes a big reactivity difference

被引:70
作者
Nyulászi, L
Hollóczki, O
Lescop, C
Hissler, M
Réau, R
机构
[1] Budapest Univ Technol & Econ, Dept Inorgan Chem, H-1521 Budapest, Hungary
[2] Univ Rennes 1, CNRS, UMR 6509, Inst Chim, F-35042 Rennes, France
关键词
D O I
10.1039/b516836h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The low aromaticity of phosphole can be switched to low antiaromaticity by oxidizing the phosphorus atom. This subtle change in the mode of delocalisation alters substantially the chemical behaviour of these heteroles.
引用
收藏
页码:996 / 998
页数:3
相关论文
共 43 条
[1]  
[Anonymous], 2001, PHOSPHOROUS CARBON H
[2]   Aromaticity as a cornerstone of heterocyclic chemistry [J].
Balaban, AT ;
Oniciu, DC ;
Katritzky, AR .
CHEMICAL REVIEWS, 2004, 104 (05) :2777-2812
[3]  
BIRD CW, 1985, TETRAHEDRON, V41, P1409, DOI 10.1016/S0040-4020(01)96543-3
[4]   PROTON [1,5] SHIFTS IN P-UNSUBSTITUTED 1H-PHOSPHOLES - SYNTHESIS AND CHEMISTRY OF 2H-PHOSPHOLE DIMERS [J].
CHARRIER, C ;
BONNARD, H ;
DELAUZON, G ;
MATHEY, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (23) :6871-6877
[5]   Nucleus-independent chemical shifts (NICS) as an aromaticity criterion [J].
Chen, ZF ;
Wannere, CS ;
Corminboeuf, C ;
Puchta, R ;
Schleyer, PV .
CHEMICAL REVIEWS, 2005, 105 (10) :3842-3888
[6]  
Cloke FGN, 1998, ANGEW CHEM INT EDIT, V37, P1083, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1083::AID-ANIE1083>3.0.CO
[7]  
2-C
[8]   Energetic aspects of cyclic Pi-electron delocalization: Evaluation of the methods of estimating aromatic stabilization energies [J].
Cyranski, MK .
CHEMICAL REVIEWS, 2005, 105 (10) :3773-3811
[9]   Facts and artifacts about aromatic stability estimation [J].
Cyranski, MK ;
Schleyer, PV ;
Krygowski, TM ;
Jiao, HJ ;
Hohlneicher, G .
TETRAHEDRON, 2003, 59 (10) :1657-1665
[10]   Structure-property relationships in phosphole-containing π-conjugated systems:: A quantum chemical study [J].
Delaere, D ;
Nguyen, MT ;
Vanquickenborne, LG .
JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (06) :838-846