scholarly journals Case for Lithium Tetramethylpiperidide-Mediated Ortholithiations: Reactivity and Mechanisms

2018 ◽  
Vol 140 (14) ◽  
pp. 4877-4883 ◽  
Author(s):  
Kyle A. Mack ◽  
David B. Collum
Keyword(s):  
Lithium Tetramethylpiperidide

ChemInform Abstract: Mixed Aggregates of Lithium Tetramethylpiperidide with Butyllithium: Stereoselectivity of Ketone Enolization.

ChemInform ◽  
2010 ◽  
Vol 29 (40) ◽  
pp. no-no
Author(s):  
Y. BALAMRAJU ◽  
C. D. SHARP ◽  
W. GAMMILL ◽  
N. MANUEL ◽  
L. M. PRATT
Keyword(s):  
Mixed Aggregates ◽  
Lithium Tetramethylpiperidide

Mixed aggregates of lithium tetramethylpiperidide with butyllithium: Stereoselectivity of ketone enolization

Tetrahedron ◽  
1998 ◽  
Vol 54 (26) ◽  
pp. 7357-7366 ◽  
Author(s):  
Yuvaraju Balamraju ◽  
Christopher D. Sharp ◽  
Wesley Gammill ◽  
Nick Manuel ◽  
Lawrence M. Pratt
Keyword(s):  
Mixed Aggregates ◽  
Lithium Tetramethylpiperidide

Acidity measurements in THF. V. Heteroaromatic compounds containing 5-membered rings

1985 ◽  
Vol 63 (12) ◽  
pp. 3505-3509 ◽  
Author(s):  
Robert R. Fraser ◽  
Tarek S. Mansour ◽  
Sylvain Savard
Keyword(s):  
Nmr Spectroscopy ◽  
Aromatic Compounds ◽  
Heteroaromatic Compounds ◽  
Aromatic Heterocycles ◽  
Nitrogen Heteroatom ◽  
Carbon Acid ◽  
C Nmr ◽  
Lithium Tetramethylpiperidide

The pKa's of 13 heterocyclic aromatic compounds have been measured in tetrahydrofuran (THF) using 13C nmr spectroscopy. The acidifying effect of a nitrogen heteroatom is seen to be quite large (4–6 pK units versus C—H) on an adjacent C—H bond but small on a more remote hydrogen. Most of these aromatic heterocycles are sufficiently acidic, pKa < 34, to be completely deprotonated by lithium tetramethylpiperidide in THF. Benzoxazole appears to be an extremely strong carbon acid, its ring-opened isomer having a pKa of less than 15.7.

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