1,2,4-Tris(trifluoromethyl)benzene: selective lithiation and subsequent electrophilic substitution
1998
Abstract
1,2,4-Tris(trifluoromethyl)benzene quant. undergoes a hydrogen/metal exchange when treated with an ethereal soln. of lithium 2,2,6,6-tetramethylpiperidide. Proton abstraction occurs concomitantly from positions 5 and 6, the ratios varying from 80:20 to 90:10, depending on the reaction conditions. Pure 5-iodo-1,2,4-tris(trifluoromethyl)benzene was readily obtained by fractional crystn. of the regioisomeric mixt. and was used to prep. 5-substituted derivs. of 1,2,4-tris(trifluoromethyl)benzene by consecutive reaction with tert-butyllithium and an electrophile. [on SciFinder (R)]
Details
Title
1,2,4-Tris(trifluoromethyl)benzene: selective lithiation and subsequent electrophilic substitution
Author(s)
Schlosser, Manfred ; Porwisiak, Jacek ; Mongin, Florence
Published in
Tetrahedron
Volume
54
Issue
5/6
Pages
895-900
Date
1998
ISSN
0040-4020
Keywords
Regiochemistry; Substitution reaction (lithiation and electrophilic substitution of tris(trifluoromethyl)benzene); Lithiation (regioselective; lithiation and electrophilic substitution of tris(trifluoromethyl)benzene); trifluoromethylbenzene regioselective lithiation electrophilic substitution; lithium tetramethylpiperidide lithiation substitution trifluoromethylbenzene
Note
CAN 128:140479
25-3
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chim. Org. Univ. Batiment Chim,Lausanne-Dorigny,Switz.
Journal
written in English.
393-05-5 (1,2,4-Tris(trifluoromethyl)benzene); 38227-87-1 (Lithium 2,2,6,6-tetramethylpiperidide) Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation and electrophilic substitution of tris(trifluoromethyl)benzene); 202465-19-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (lithiation and electrophilic substitution of tris(trifluoromethyl)benzene); 202465-23-4P; 202465-24-5P Role: SPN (Synthetic preparation), PREP (Preparation) (lithiation and electrophilic substitution of tris(trifluoromethyl)benzene); 202465-18-7P; 202465-20-1P; 202465-21-2P; 202465-22-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
25-3
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chim. Org. Univ. Batiment Chim,Lausanne-Dorigny,Switz.
Journal
written in English.
393-05-5 (1,2,4-Tris(trifluoromethyl)benzene); 38227-87-1 (Lithium 2,2,6,6-tetramethylpiperidide) Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation and electrophilic substitution of tris(trifluoromethyl)benzene); 202465-19-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (lithiation and electrophilic substitution of tris(trifluoromethyl)benzene); 202465-23-4P; 202465-24-5P Role: SPN (Synthetic preparation), PREP (Preparation) (lithiation and electrophilic substitution of tris(trifluoromethyl)benzene); 202465-18-7P; 202465-20-1P; 202465-21-2P; 202465-22-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Laboratories
LSCO
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2006-03-03