N-Phenylpyrrole: a kinetic, though not thermodynamic preference for dilithiation
Faigl, Ferenc; Schlosser, Manfred
1993

Abstract

Under appropriate conditions the clean prepn. of either the a-mono-lithiated or the o,a-dilithiated deriv. of N-phenylpyrrole is possible. In the latter case, the first deprotonation occurs at the a-position. Dimetalation is kinetically but not thermodynamically favored. [on SciFinder (R)]

Details

Title N-Phenylpyrrole: a kinetic, though not thermodynamic preference for dilithiation
Author(s) Faigl, Ferenc ; Schlosser, Manfred
Published in Tetrahedron
Volume 49
Issue 45
Pages 10271-8
Date 1993
ISSN 0040-4020
Keywords
Note CAN 120:216576
22-12
Physical Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
109-72-8 (Butyllithium); 110-18-9 (TMEDA); 635-90-5 (1-Phenylpyrrole); 865-47-4 (Potassium tert-butoxide) Role: RCT (Reactant), RACT (Reactant or reagent) (dilithiation of phenylpyrrole with amine-activated butyllithium: kinetic control); 10333-67-2P; 35524-54-0P; 38278-63-6P; 50691-32-2P; 78540-03-1P; 154245-22-4P; 154245-23-5P; 154245-24-6P; 154245-25-7P; 154245-26-8P; 154245-27-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., dilithiation of phenylpyrrole with amine-activated butyllithium: kinetic control)
DOI https://doi.org/10.1016/S0040-4020(01)80556-1
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
Record creation date 2006-03-03