1-CHLORO-2,2-BIS(4-CHLOROPHENYL)-1-LITHIOETHENE.TMEDA.2 THF - STRUCTURE OF A LI-CL CARBENOID

被引:78
作者
BOCHE, G
MARSCH, M
MULLER, A
HARMS, K
机构
[1] Fachbereich Chemie, Universität Marburg, D-35032, Harns‐Meerwein‐Strasse
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 07期
关键词
D O I
10.1002/anie.199310321
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The ClCl bond in the carbenoid 1 is about 12 pm longer than that in the compound containing a H atom in place of the Li substituent. This explains the facile reaction of carbenoids with the nucleophiles RLi. The X‐ray crystal structure of 1 is consistent with 13C‐NMR data, as well as with the stereochemistry of reactions of carbenoids with RLi or the Fritsch–Buttenberg–Wiechell rearrangement of vinyl carbenoids. (Figure Presented.) Copyright © 1993 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:1032 / 1033
页数:2
相关论文
共 41 条
[1]  
Allen F. H., 1992, INT TABLES CRYSTALLO, VC, P696
[2]  
[Anonymous], 1967, ANGEW CHEM, V79, P15
[3]   ALPHA-OXYGEN-SUBSTITUTED ORGANOLITHIUM COMPOUNDS AND THEIR CARBENOID NATURE - CALCULATIONS OF THE CONFIGURATIONAL STABILITY AND OF LICH2OH MODEL STRUCTURES, CRYSTAL-STRUCTURE OF DIPHENYL(TRIMETHYLSILYLOXY)METHYLLITHIUM.3 THF, AND THE STEREOCHEMISTRY OF THE (REVERSE) BROOK REARRANGEMENT [J].
BOCHE, G ;
OPEL, A ;
MARSCH, M ;
HARMS, K ;
HALLER, F ;
LOHRENZ, JCW ;
THUMMLER, C ;
KOCH, W .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (10) :2265-2273
[4]   THE STRUCTURE OF LITHIUM COMPOUNDS OF SULFONES, SULFOXIMIDES, SULFOXIDES, THIOETHERS AND 1,3-DITHIANES, NITRILES, NITRO-COMPOUNDS AND HYDRAZONES [J].
BOCHE, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (03) :277-297
[5]  
BOCHE G, IN PRESS
[6]  
BOCHE G, 1989, ANGEW CHEM, V101, P286
[8]   CARBENOID, CCL3LI, ESCHEWS TETRAHEDRAL STRUCTURES [J].
CLARK, T ;
SCHLEYER, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (26) :7747-7748
[9]   STRUCTURES OF THE CARBENOID CH2FLI - ABINITIO MO CALCULATIONS [J].
CLARK, T ;
SCHLEYER, PV .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (20) :883-884
[10]  
CLARK T, 1979, TETRAHEDRON LETT, P4963