N-Phenylpyrrole: a kinetic, though not thermodynamic preference for dilithiation

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)]


Published in:
Tetrahedron, 49, 45, 10271-8
Year:
1993
Keywords:
Note:
CAN 120:216576
22-12
Physical Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4020
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)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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