AN UNUSUAL GAMMA-SILYL EFFECT IN TICL4-CATALYZED ARYLATION OF 1,4-BENZOQUINONES

被引:19
作者
ENGLER, TA
REDDY, JP
机构
[1] Department of Chemistry, University of Kansas, Lawrence
关键词
D O I
10.1021/jo00023a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclopropylbenzene (1c) reacts with 2-methoxy-1,4-benzoquinone in the presence of TiCl4 to give 2-(4'-cyclopropylphenyl)-5-methoxy-1,4-benzoquinone in moderate yield (46%). Considerable improvement in yield (69%) is observed in reactions of trans-2-phenyl-1-(trimethylsilyl)cyclopropane (1a) with the TiCl4-quinone complex.
引用
收藏
页码:6491 / 6494
页数:4
相关论文
共 35 条
[1]  
BASSINDALE AR, 1989, CHEM ORGANIC SILICON, V1, pCH14
[2]   GEOMETRICAL DEPENDENCE OF GAMMA-TRIMETHYLSILYL GROUPS ON NORBORNYL SOLVOLYSES - RAPID-INJECTION KINETIC METHODS FOR SOLVOLYSES OF UNSTABLE MESYLATES [J].
BENTLEY, TW ;
KIRMSE, W ;
LLEWELLYN, G ;
SOLLENBOHMER, F .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1536-1540
[3]   THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].
BRINGMANN, G ;
WALTER, R ;
WEIRICH, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991
[4]   REACTIONS OF QUINONES WITH AROMATIC ETHERS .7. TRIPHENYLENE-1,4=5,8-DIQUINONES FROM REACTIONS OF VERATROLE OR 3,4-DIMETHOXYPHENYL-BENZOQUINONES WITH BENZOQUINONES [J].
BUCHAN, R ;
MUSGRAVE, OC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (21) :2185-2189
[5]   SYNTHESIS OF SOME ARYLATED QUINONES [J].
CAMERON, DW ;
FEUTRILL, GI ;
PATTI, AF ;
PERLMUTTER, P ;
SEFTON, MA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (07) :1501-1508
[6]  
CHOUDARY BM, 1986, INDIAN J CHEM B, V25, P1159
[7]   REACTIONS OF DITHIANE DERIVED ALCOHOLS - PROMOTION OF THE THORPE-INGOLD EFFECT BY TRIMETHYLSILYL AND TERT-BUTYL SUBSTITUENTS [J].
DAVEY, AE ;
PARSONS, AF ;
TAYLOR, RJK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (10) :1853-1858
[8]   GAMMA-SILICON STABILIZATION OF CARBONIUM-IONS [J].
DAVIDSON, ER ;
SHINER, VJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :3135-3137
[9]  
DELUCCA G, 1983, TETRAHEDRON LETT, P4931
[10]   ARYLATION REACTIONS WITH ORGANOBISMUTH REAGENTS [J].
FINET, JP .
CHEMICAL REVIEWS, 1989, 89 (07) :1487-1501