N-PHENYLPYRROLE - A KINETIC, THOUGH NOT THERMODYNAMIC PREFERENCE FOR DILITHIATION

被引：32

作者：

FAIGL, F ^{[1
]}

SCHLOSSER, M ^{[1
]}

机构：

[1] UNIV LAUSANNE,INST CHIM ORGAN,RUE BARRE 2,CH-1005 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 45期

关键词：

D O I：

10.1016/S0040-4020(01)80556-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under appropriate conditions the clean preparation of either the alpha-monolithiated or the o,alpha-dilithiated derivative of N-phenylpyrrole is possible. In the latter case, the first deprotonation occurs at the alpha-position. Dimetalation is kinetically but not thermodynamically favored.

引用

页码：10271 / 10278

页数：8

共 18 条

[1] 2-LITHIO-1-PHENYLPYRROLE - X-RAY STRUCTURE-ANALYSIS AND LI-6-H-1 2D HETERONUCLEAR OVERHAUSER NMR-SPECTROSCOPY (2D HOESY) [J].

BAUER, W ;

MULLER, G ;

PI, R ;

SCHLEYER, PV .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (12) :1103-1104

[2]

BAUER W, 1986, ANGEW CHEM, V98, P1130

[3]

CHADWICK DJ, 1979, J CHEM SOC PERK T 1, P2845, DOI 10.1039/p19790002845

[4] LITHIATIONS OF 1-TRIALKYLSILYLPYRROLES - N TO C SILYL GROUP REARRANGEMENT [J].

CHADWICK, DJ ;

HODGSON, ST .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (08) :1833-1836

[5] PREPARATION AND REACTIVITY OF 2,2'-DILITHIO-1-PHENYLPYRROLE [J].

CHEESEMAN, GWH ;

GREENBERG, SG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 166 (02) :139-152

[6] N-NITROMETHYLPHTHALIMIDE - FORMYL ANION EQUIVALENT [J].

COWHERD, FG ;

DORIA, MC ;

GALEAZZI, E ;

MUCHOWSKI, JM .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (16) :2919-2929

[7]

GHARPURE M, 1991, SYNTHESIS-STUTTGART, P1079

[8] N-FUNCTIONALLY SUBSTITUTED PYRROLES [J].

JOSEY, AD ;

JENNER, EL .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (07) :2466-&

[9]

MARXER A, 1974, HELV CHIM ACTA, V57, P1989

[10] PALLADIUM-PHOSPHINE COMPLEX CATALYZED CROSS-COUPLING REACTION OF 1-METHYL-2-PYRROLYL-MAGNESIUM BROMIDE AND ZINC-CHLORIDE WITH ORGANIC HALIDES [J].

MINATO, A ;

TAMAO, K ;

HAYASHI, T ;

SUZUKI, K ;

KUMADA, M .

TETRAHEDRON LETTERS, 1981, 22 (52) :5319-5322

← 1 2 →