INTRAMOLECULAR ANODIC OLEFIN COUPLING REACTIONS - THE USE OF ALLYSILANES

被引:10
作者
MOELLER, KD
HUDSON, CM
机构
[1] Department of Chemistry, Washington University, St. Louis
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)79910-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of allylsilanes as directing groups in the intramolecular electrochemical coupling of electron rich olefins has been examined. The allylsilanes were shown to provide an effective means for controlling product selectivity, and led to the formation of five- and six-membered ring products in 59-84% isolated yields.
引用
收藏
页码:2307 / 2310
页数:4
相关论文
共 16 条
[1]   ANODIC-OXIDATION OF ORGANIC-COMPOUNDS .21. ANODIC-OXIDATION OF CONJUGATED DIENES [J].
BALTES, H ;
STECKHAN, E ;
SCHAFER, HJ .
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (04) :1294-1314
[2]   ANODIC-OXIDATION .11. CARBON ANODES IN ELECTROSYNTHESES BASED ON CARBOXYLATE IONS [J].
BRENNAN, MPJ ;
BRETTLE, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (03) :257-261
[3]  
ENGELS R, 1977, LIEBIGS ANN CHEM, P2104
[4]  
Fleming I., 1979, COMPREHENSIVE ORGANI, V3, P541
[5]   ANODIC DIMERIZATION OF ENOL ETHERS [J].
KOCH, D ;
SCHAFER, H ;
STECKHAN, E .
CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (11) :3640-3657
[6]   ANODIC-OXIDATION OF (TRIMETHYLSILYL)METHANES WITH PI-ELECTRON SUBSTITUENTS IN THE PRESENCE OF NUCLEOPHILES [J].
KOIZUMI, T ;
FUCHIGAMI, T ;
NONAKA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (01) :219-225
[7]  
LUND H, 1983, ORGANIC ELECTROCHEMI, P183
[8]   GENERATION OF ORGANIC CATIONS FROM GROUP-14 ORGANOMETALLIC COMPOUNDS VIA PHOTOINDUCED ELECTRON-TRANSFER IN THE PRESENCE OF CU(II) SALT [J].
MIZUNO, K ;
YASUEDA, M ;
OTSUJI, Y .
CHEMISTRY LETTERS, 1988, (02) :229-232
[9]   OXIDATIVE ORGANIC ELECTROCHEMISTRY - A NOVEL INTRAMOLECULAR COUPLING OF ELECTRON-RICH OLEFINS [J].
MOELLER, KD ;
MARZABADI, MR ;
NEW, DG ;
CHIANG, MY ;
KEITH, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (16) :6123-6124
[10]  
MOELLER KD, IN PRESS ELECTROORGA