SILANES IN ORGANIC-SYNTHESIS .6. CONVERSION OF UNSUBSTITUTED AND 2-ARYL KETONES TO (1-ARYLALLYL)SILANES

被引：14

作者：

FRISTAD, WE ^{[1
]}

HAN, YK ^{[1
]}

PAQUETTE, LA ^{[1
]}

机构：

[1] OHIO STATE UNIV,EVANS CHEM LABS,COLUMBUS,OH 43210

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1979年 / 174卷 / 01期

关键词：

D O I：

10.1016/S0022-328X(00)96159-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Treatment of 2- or 3-phenyl ketone arenesulfonylhydrazones with excess n-butyllithium in TMEDA at 50-60° for 2-3 h, followed by the addition of chlorotrimethylsilane, gives (1-arylallyl)silanes. Although the method has limitations, its simplicity and the availability of a companion procedure for the direct α-arylation of ketones provide desirable advantages. A number of electrophilic reactions are examined in an effort assess competitive benzylic resonance stabilization and CSi bond hyperconjugation in cyclic systems where stereoelectronic considerations also prevail. © 1979.

引用

页码：27 / 40

页数：14

共 72 条

[1]

ABEL EW, 1975, J ORGANOMET CHEM, V84, P199, DOI 10.1016/S0022-328X(00)90032-9

[2]

ABRAHAM RJ, 1970, ORG MAGN RESONANCE, V2, P173

[3] CONFORMATIONAL-ANALYSIS OF CIS-BICYCLO (4.1.0) HEPTANE DERIVATIVES .1. [J].