STEREOCHEMISTRY OF REACTIONS IN 1,2-DIMETHYLSILACYCLOPENTANE RING-SYSTEM .2. STEREOSELECTIVE TRANSFORMATION

被引:13
作者
DUBAC, J [1 ]
MAZEROLLES, P [1 ]
JOLY, M [1 ]
CARTLEDGE, FK [1 ]
WOLCOTT, JM [1 ]
机构
[1] LOUISIANA STATE UNIV,DEPT CHEM,BATON ROUGE,LA 70803
关键词
D O I
10.1016/S0022-328X(00)83441-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A number of stereoselective reactions of 1-substituted-1,2-dimethylsilacyclopentanes are described. Reactions of the silyl chloride (II) with ZnF2 and with alcohols catalyzed by amines are stereoselective as a result of rapid isomerization of II. Alcoholysis of silicon hydride (I) catalyzed by transition metals is apparently an inversion reaction regardless of the nature of the catalyst, but can appear to be stereoselective because of isomerization of alkoxysilane product. Reduction of silyl fluoride (IV) by lithium aluminum hydride is nonstereoselective, a result which is proposed to arise through rapid isomerization of intermediates with expanded coordination. © 1978.
引用
收藏
页码:203 / 221
页数:19
相关论文
共 32 条
[1]   NUCLEOPHILIC SUBSTITUTION AT SILICON - REACTION OF TRIPHENYSILYL CHLORIDE WITH 2-PROPANOL IN CCL4 [J].
ALLEN, AD ;
LAVERY, SJ .
CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (08) :1263-&
[2]   NUCLEOPHILIC SUBSTITUTION REACTIONS OF ORGANOSILICON COMPOUNDS .1. REACTIONS OF TRIISOPROPYLSILYL CHLORIDE [J].
ALLEN, AD ;
CHARLTON, JC ;
EABORN, C ;
MODENA, G .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (AUG) :3668-3670
[3]   NUCLEOPHILIC SUBSTITUTION REACTIONS OF ORGANOSILICON COMPOUNDS .2. REACTION MECHANISMS OF SOME STERICALLY HINDERED ORGANOSILICON CHLORIDES [J].
ALLEN, AD ;
MODENA, G .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (AUG) :3671-3678
[4]   SOLVENT-CATALYZED CIS-TRANS ISOMERIZATION OF HALOSILACYCLO-BUTANES AND HALOSILACYCLO-PENTANES - EVIDENCE FOR CATIONIC INTERMEDIATES WITH EXPANDED COORDINATION [J].
CARTLEDGE, FK ;
MCKINNIE, BG ;
WOLCOTT, JM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 118 (01) :7-18
[5]  
CARTLEDGE FK, 1975, TETRAHEDRON LETT, P3593
[6]  
CARTLEDGE FK, 1977, J ORGANOMETAL CHEM
[7]   PREPARATION, RESOLUTION AND DYNAMIC STEREOCHEMISTRY OF 7H-7-METHYL-7-SILABENZ[D,E]ANTHRACENE SYSTEM [J].
CITRON, JD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 86 (03) :359-367
[8]  
CORRIU JP, 1974, J ORGANOMETAL CHEM, V64, P351
[9]  
CORRIU R, 1972, B SOC CHIM FR, P1490
[10]  
CORRIU R, 1969, B SOC CHIM FR, P3491