Dizincation and dimagnesiation of benzene using alkali-metal-mediated metallation

被引:53
作者
Armstrong, David R.
Clegg, William
Dale, Sophie H.
Graham, David V.
Hevia, Eva
Hogg, Lorna M.
Honeyman, Gordon W.
Kennedy, Alan R.
Mulvey, Robert E. [1 ]
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XN, Lanark, Scotland
[2] Univ Newcastle Upon Tyne, Sch Nat Sci Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
关键词
D O I
10.1039/b613655a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Benzene can be easily 1,4-dideprotonated stoichiometrically on reaction with two equivalents of a synergic mixture of (Bu2Zn)-Bu-t, NaTMP and TMEDA to give a unique 1,4-dizincated benzene product which has been characterised by X-ray crystallography and NMR spectroscopy as well as modelled theoretically by DFT computational studies; a related synergic dimagnesiation of benzene is also reported.
引用
收藏
页码:598 / 600
页数:3
相关论文
共 11 条
[1]   Sodium dialkyl-amidozincates: Alkyl or amido bases? An experimental and theoretical case study [J].
Andrikopoulos, PC ;
Armstrong, DR ;
Barley, HRL ;
Clegg, W ;
Dale, SH ;
Hevia, E ;
Honeyman, GW ;
Kennedy, AR ;
Mulvey, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6184-6185
[2]  
Armstrong DR, 1999, ANGEW CHEM INT EDIT, V38, P131, DOI 10.1002/(SICI)1521-3773(19990115)38:1/2<131::AID-ANIE131>3.0.CO
[3]  
2-9
[4]  
Baston E, 2001, EUR J ORG CHEM, V2001, P3985
[5]  
BECK P, 1982, ACCOUNTS CHEM RES, V15, P306
[6]   Macrocyclic polyethers as probes to assess and understand alkali metal cation-π interactions [J].
Gokel, GW ;
Barbour, LJ ;
De Wall, SL ;
Meadows, ES .
COORDINATION CHEMISTRY REVIEWS, 2001, 222 :127-154
[7]  
Gschwend H. W., 1979, ORG REACTIONS, P1
[8]  
Hartung C. G., 2002, MODERN ARENE CHEM, V34, P330, DOI DOI 10.1002/3527601767.CH10
[9]  
Knochel P., 1999, ORGANOZINC REAGENTS
[10]   Modern ate chemistry: Applications of synergic mixed alkali-metal-magnesium or -zinc reagents in synthesis and structure building [J].
Mulvey, RE .
ORGANOMETALLICS, 2006, 25 (05) :1060-1075