Formation of 2-substituted iodobenzenes from iodobenzene via benzyne and ate complex intermediates

被引:42
作者
Tripathy, S [1 ]
LeBlanc, R [1 ]
Durst, T [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
关键词
D O I
10.1021/ol991129k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The generation of benzyne from iodobenzene with lithium tetramethylpiperidide in THF at -40 degrees C in the presence of lithium amides and ester enolates leads to mixtures in which 2-substituted iodobenzenes are often the major products, These products are obtained by iodine transfer from iodobenzene to the intermediate 2-lithioaromatics. The transfer of iodine occurs via a hypervalent iodine (ate) complex.
引用
收藏
页码:1973 / 1975
页数:3
相关论文
共 5 条
[1]   A RAPID, CONVERGENT, AND REGIOSELECTIVE SYNTHESIS OF ANTHRACENES [J].
FITZGERALD, JJ ;
DRYSDALE, NE ;
OLOFSON, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7122-7126
[2]  
LEBLANC R, 1999, THESIS U OTTAWA
[3]   USEFUL SYNTHESIS OF ARYLCYCLOPROPANES [J].
OLOFSON, RA ;
DOUGHERT.CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :581-582
[4]   THE LITHIUM-METALLOID EXCHANGE-REACTION - NMR-STUDIES OF THE PHENYLLITHIUM-IODOBENZENE EXCHANGE [J].
REICH, HJ ;
GREEN, DP ;
PHILLIPS, NH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3444-3445
[5]   LITHIUM-METALLOID EXCHANGE-REACTIONS - KINETIC EVIDENCE FOR AN INTERMEDIATE IN THE LITHIUM IODINE EXCHANGE [J].
REICH, HJ ;
PHILLIPS, NH ;
REICH, IL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :4101-4103