The acidifying effects of chlorine and bromine: Little difference

被引：57

作者：

Mongin, F ^{[1
]}

Schlosser, M ^{[1
]}

机构：

[1] UNIV LAUSANNE,INST CHIM ORGAN,CH-1015 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(97)00131-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium diisopropylamide deprotonates ortho- and para-bromochlorobenzene randomly at the two halogen adjacent positions. Obviously for steric reasons, the bulkier base lithium 2,2,6,6-tetramethylpiperidide favors the attack in the vicinity of the chlorine rather than the bromine atom to the extent of 2 : 1. - At -75 degrees C, both 2-bromo-3-chlorophenyllithium and 3-bromo-2-chlorophenyllithium isomerize to give 2-bromo-6-chlorophenyllithium. The latter species can be directly generated from 1-bromo-3-chlorobenzene. (C) 1997 Elsevier Science Ltd.

引用

页码：1559 / 1562

页数：4

共 15 条

[1] THE BROMINATION OF ACRIDONE [J].

ACHESON, RM ;

ROBINSON, MJT .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (JAN) :232-238

[2]

[Anonymous], 1994, PROG HETEROCYCL CHEM

[3] Saponification of substituted benzanilide. [J].

Asinger, F .

JOURNAL FUR PRAKTISCHE CHEMIE-LEIPZIG, 1935, 142 (11/12) :291-300

[4] RELATIONSHIPS BETWEEN THE THERMODYNAMICS OF PROTONATION IN THE GAS AND AQUEOUS PHASE FOR 2-SUBSTITUTED, 3-SUBSTITUTED, AND 4-SUBSTITUTED PYRIDINES [J].

AUE, DH ;

WEBB, HM ;

DAVIDSON, WR ;

TOURE, P ;

HOPKINS, HP ;

MOULIK, SP ;

JAHAGIRDAR, DV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1770-1780

[5] BASE-CATALYZED HALOGEN DANCE, AND OTHER REACTIONS OF ARYL HALIDES [J].

BUNNETT, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 1972, 5 (04) :139-&

[6] 1,3,5-TRISUBSTITUTED BENZENES .1. SYNTHESIS AND REACTIONS OF 3,5-DIBROMOPHENYLLITHIUM [J].

CHEN, LS ;

CHEN, GJ ;

TAMBORSKI, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 215 (03) :281-291

[7] DERIVATIVES OF 6-AMINOPENICILLANIC ACID .5. ANALOGUES OF 2,6-DIMETHOXYPHENYLPENICILLIN WITH ENHANCED STABILITY TOWARDS ACIDS [J].

DOYLE, FP ;

WADDINGTON, HRJ ;

HANSON, JC ;

NAYLER, JHC ;

THOMAS, GR .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (JAN) :497-&

[8] COPPER(I) CATALYZED REPLACEMENT OF BROMINE BY CHLORIDE-ION IN BROMOBENZOIC ACIDS [J].

LIEDHOLM, B .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (08) :713-715

[9] Reagent-modulated optional site selectivities: The metalation of o-, m- and p-halobenzotrifluorides [J].

Mongin, F ;

Desponds, O ;

Schlosser, M .

TETRAHEDRON LETTERS, 1996, 37 (16) :2767-2770

[10]

Moyroud J, 1996, B SOC CHIM FR, V133, P133

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