ELECTRONIC EFFECTS AND MECHANISTIC FEATURES IN THE REARRANGEMENT-DISPLACEMENT REACTIONS OF ARYL(CHLOROMETHYL)DIPHENYLSILANES WITH FLUORIDE-ION

被引:11
作者
APRAHAMIAN, SL [1 ]
SHECHTER, H [1 ]
机构
[1] OHIO STATE UNIV,DEPT CHEM,COLUMBUS,OH 43210
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(00)88733-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
At 25°C aryl migrations from negatively-charged pentacoordinate silicon correlate with the abilities of the rearranging groups to bear negative charge, but at lower temperatures the migrations become less dependent on electron-withdrawing stabilization. © 1990.
引用
收藏
页码:1089 / 1092
页数:4
相关论文
共 20 条
[1]   REACTIONS OF FLUORIDE-ION SOURCES WITH HALOALKYL DERIVATIVES OF PHENAZASILINES AND PHENOXASILINS [J].
COREY, JY ;
COREY, ER ;
CHANG, VHT ;
HAUSER, MA ;
LEIBER, MA ;
REINSEL, TE ;
RIVA, ME .
ORGANOMETALLICS, 1984, 3 (07) :1051-1060
[2]  
CORRIU R, 1984, TOP STEREOCHEM, V15, P357
[3]   NUCLEOPHILIC DISPLACEMENT AT SILICON STEREOCHEMISTRY AND MECHANISTIC IMPLICATIONS [J].
CORRIU, RJP ;
GUERIN, C .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 198 (03) :231-320
[4]   FLUORIDE-ION INDUCED REARRANGEMENTS OF CHLOROMETHYL-SUBSTITUTED SILANES [J].
DAMRAUER, R ;
YOST, VE ;
DANAHEY, SE ;
OCONNELL, BK .
ORGANOMETALLICS, 1985, 4 (10) :1779-1784
[5]   FLUORIDE-ION INDUCED REARRANGEMENTS OF CHLOROMETHYL-SUBSTITUTED SILANES - CARBANIONIC CHARACTER OF GROUPS UNDERGOING MIGRATION [J].
DAMRAUER, R ;
DANAHEY, SE ;
YOST, VE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (24) :7633-7634
[6]  
EABORN C, 1955, CHEM IND-LONDON, P1041
[7]   ORGANOSILICON COMPOUNDS .18. THE INTERACTION OF (ARYLDIMETHYLSILYL)METHYL CHLORIDES AND SODIUM ETHOXIDE IN ETHANOL [J].
EABORN, C ;
JEFFREY, JC .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (JAN) :137-144
[8]   MARKED MEDIUM EFFECTS ON THE SUBSTITUTION AND THE ADDITION-REARRANGEMENT-EJECTION REACTIONS OF (HALOMETHYL)SILANES WITH METHOXIDES [J].
KREEGER, RL ;
MENARD, PR ;
SANS, EA ;
SHECHTER, H .
TETRAHEDRON LETTERS, 1985, 26 (09) :1115-1118
[9]   REACTIONS OF (CHLOROMETHYL)PENTAMETHYLDISILANE WITH SOME NUCLEOPHILIC REAGENTS [J].
KUMADA, M ;
ISHIKAWA, M ;
TAMAO, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1966, 5 (03) :226-&
[10]   THE SYNTHESIS AND REACTIONS OF CERTAIN DISILANES CONTAINING CHLOROMETHYL GROUPS [J].
KUMADA, M ;
ISHIKAWA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1964, 1 (05) :411-419