Reactions of dilithiobutadienes with monochlorosilanes: Observation of facile loss of organic groups from silicon

被引:45
作者
Hudrlik, PF [1 ]
Dai, DH [1 ]
Hudrlik, AM [1 ]
机构
[1] Howard Univ, Dept Chem, Washington, DC 20059 USA
基金
美国国家科学基金会;
关键词
silole; chlorosilane; dilithiobutadiene; organosilicon; pentacoordinate silicon;
D O I
10.1016/j.jorganchem.2005.11.068
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reactions of 1,4-dilithiobutadieties (from 1,4-diiodo-1,2,3,4-tetraethylbutidiene (1) and 2,2'-dibromobiphenyl (7) with t-BuLi) with Me3SiCl gave siloles (3 and 9a) as the major products. No evidence for a disilylated butadiene was obtained. Use of higher molecular weight chlorosilanes ((allyl)Me2SiCl, BnMe2SiCl, and PhMe2SiCl) with dibromide 7 gave dimethylsilole 9a and a silane (10a, 10b, or 10c) resulting from trapping of the organic group by the chlorosilane. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:1257 / 1264
页数:8
相关论文
共 67 条
[1]   1,4-DILITHIO-1,3-BUTADIENES [J].
ASHE, AJ ;
MAHMOUD, S .
ORGANOMETALLICS, 1988, 7 (08) :1878-1880
[2]   SECONDARY BONDING IN ORGANOPNICOGEN COMPOUNDS - COMPARISON OF THE STRUCTURES OF OCTAMETHYL-1,1'-DISTIBAFERROCENE AND OCTAMETHYL-1,1'-DIARSAFERROCENE [J].
ASHE, AJ ;
KAMPF, JW ;
PILOTEK, S ;
ROUSSEAU, R .
ORGANOMETALLICS, 1994, 13 (10) :4067-4071
[3]  
BALLWEG D, 2002, SILICON CHEM, V0001
[4]  
BANKWITZ U, 1995, J ORGANOMET CHEM, V499, P7
[5]   A controlled, iterative synthesis and the electronic properties of oligo[(p-phenyleneethynylene)-alt-(2,5-slioleneethynylene)]s [J].
Boydston, AJ ;
Yin, YS ;
Pagenkopf, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10350-10354
[6]   SELECTIVE, ZIRCONIUM-MEDIATED CROSS-COUPLING OF ALKYNES - SYNTHESIS OF ISOMERICALLY PURE 1,3-DIENES AND 1,4-DIIODO 1,3-DIENES [J].
BUCHWALD, SL ;
NIELSEN, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2870-2874
[7]   Synthesis and characterization of dibenzannulated silole dianions.: The 1,1-dilithiosilafluorene and 1,1′-dilithiobis(silafluorene) dianions [J].
Choi, SB ;
Boudjouk, P .
TETRAHEDRON LETTERS, 2000, 41 (35) :6685-6688
[8]   Aromatic benzannulated silole dianions. The dilithio and disodio salts of a silaindenyl dianion [J].
Choi, SB ;
Boudjouk, P ;
Wei, PR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) :5814-5815
[9]   REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].
CHUIT, C ;
CORRIU, RJP ;
REYE, C ;
YOUNG, JC .
CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448
[10]   GROUP-14 METALLOLES .2. IONIC SPECIES AND COORDINATION-COMPOUNDS [J].
COLOMER, E ;
CORRIU, RJP ;
LHEUREUX, M .
CHEMICAL REVIEWS, 1990, 90 (01) :265-282