METALATION REACTIONS .16. POLYLITHIATION OF 1,3,5-TRIMETHOXYBENZENE AND 1,2,4-TRIMETHOXYBENZENE

被引:11
作者
CABIDDU, S
CONTINI, L
FATTUONI, C
FLORIS, C
GELLI, G
机构
[1] Dipartimento di Scienze Chimiche, Università, I-09124 Cagliari, Via Ospedale
关键词
D O I
10.1016/S0040-4020(01)96216-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polylithiation reactions of 1,3,5- and 1,2,4-trimethoxybenzenes have been investigated. Results showed that it is possible to substitute all arylic hydrogens through one-pot sequential bimetalation/monometalation, monometalation/bimetalation or three monometalations. This reaction is strongly affected by steric hindrance.
引用
收藏
页码:9279 / 9288
页数:10
相关论文
共 28 条
[1]   HOMOGENEOUS METALATION OF ALKYLBENZENES [J].
BROADDUS, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (01) :10-&
[2]   METALATIONS OF ALKOXYALKYLTHIOBENZENES [J].
CABIDDU, S ;
MELIS, S ;
PIRAS, PP ;
SECCI, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 132 (03) :321-326
[3]  
CABIDDU S, 1981, GAZZ CHIM ITAL, V111, P123
[4]   METALATION REACTIONS .14. REGIOSPECIFIC PREPARATION OF POLYSUBSTITUTED BENZENES VIA MONO-LITHIATION OR DI-LITHIATION REACTIONS OF AROMATIC THIOETHERS [J].
CABIDDU, S ;
FATTUONI, C ;
FLORIS, C ;
GELLI, G ;
MELIS, S ;
SOTGIU, F .
TETRAHEDRON, 1990, 46 (03) :861-884
[5]  
CABIDDU S, 1986, TETRAHEDRON LETT, V38, P4625
[6]   DILITHIATION OF AROMATIC ETHERS [J].
CROWTHER, GP ;
SUNDBERG, RJ ;
SARPESHKAR, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (24) :4657-4663
[7]   COMPLEXATION AS A FACTOR IN METALATION REACTIONS - METALATION OF 1-METHOXY-2-PHENOXYETHANE [J].
ELLISON, RA ;
KOTSONIS, FN .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (24) :4192-4196
[8]   ORTHO LITHIATION OF MONOSUBSTITUTED BENZENES - A QUANTITATIVE-DETERMINATION OF PKA VALUES IN TETRAHYDROFURAN [J].
FRASER, RR ;
BRESSE, M ;
MANSOUR, TS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) :7790-7791
[9]   The quantitative analysis of alkyllithium compounds [J].
Gilman, H ;
Haubein, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1515-1516
[10]  
Gschwend H.W., 1979, ORG REACT, V26, P1