1,8-DIFUNCTIONALIZED NAPHTHALENES AS BUILDING-BLOCKS - CONVENIENT LOW-TEMPERATURE SYNTHESIS OF 1-SILAACENAPHTHENES

被引:15
作者
KIELY, JS [1 ]
BOUDJOUK, P [1 ]
机构
[1] N DAKOTA STATE UNIV,DEPT CHEM,FARGO,ND 58102
关键词
D O I
10.1016/S0022-328X(00)94380-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of 1-silaacenaphthenes by the reaction of chlorosilanes with 8-bromo-1-halomethylnaphthalenes and magnesium is described. The use of dichlorosilanes was found to give better yields of 1-silaacenaphthenes than trichlorosilanes. Halogen-metal exchange between 8-bromo-1-halomethylnapthalenes and n-butyllithium was also investigated as a method of preparing 1-silaacenaphthenes. 1,1,2,2-Tetramethyl-1-silaacenaphthene was synthesized from 8-bromo-1-iodonapthalene in good yield. © 1979.
引用
收藏
页码:173 / 183
页数:11
相关论文
共 25 条
[1]   COMPETITION OF FLUORENE OR BROMOBENZENE WITH TRIMETHYLCHLOROSILANE FOR N-BUTYLLITHIUM [J].
BEY, AE ;
WEYENBER.DR .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (06) :2036-&
[2]   ORGANOSILICON COMPOUNDS .53. 1,1,2,2-TETRAMETHYL-1,2-DISILA-4-CYCLOHEXENE [J].
BIRKOFER, L ;
WENIGER, W .
CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (11) :3595-3600
[3]  
CHERNYSHEV EA, 1975, ZH OBSHCH KHIM+, V45, P2223
[4]  
CHERNYSHEV EA, 1971, ZH OBSHCH KHIM+, V41, P122
[5]  
CHERNYSHEV EA, 1976, ZH OBSHCH KHIM+, V46, P1278
[6]  
CHERNYSHEV EA, 1970, ZH OBSHCH KHIM+, V40, P1052
[7]   ORGANOSILICON COMPOUNDS .40. RATES OF RING-OPENING OF SOME BENZOSILACYCLOALKENES [J].
EABORN, C ;
WALTON, DRM ;
CHAN, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 9 (02) :251-&
[8]   LITHIATIONS OF ALPHA- AND BETA-DIMETHYLAMINOMETHYLNAPHTHALENES WITH N-BUTYLLITHIUM AND CONDENSATIONS WITH BENZOPHENONE . SOME RELATED RESULTS [J].
GAY, RL ;
HAUSER, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (10) :2297-&
[9]   SYNTHESIS OF SOME DIPHENYL AND TRIPHENYL DERIVATIVES OF ANTHRACENE AND NAPHTHALENE [J].
HOUSE, HO ;
CAMPBELL, WJ ;
KOEPSELL, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (07) :1003-&
[10]   SYNTHESIS OF TERMINAL ARYLACETYLENES - INSITU GENERATED COPPER(I) ACETYLIDE [J].
KIELY, JS ;
BOUDJOUK, P ;
NELSON, LL .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (15) :2626-2629