38227-87-1

Usage

Uses

Used in Chemical Synthesis:
LITHIUM TETRAMETHYLPIPERIDIDE is used as a strong base for the synthesis of enamines from terminal epoxides through trans-α-lithiated epoxide as an intermediate. This application takes advantage of LTMP's ability to deprotonate epoxides, leading to the formation of enamines, which are valuable intermediates in organic chemistry.
Used in Ortholithiation of Arenes:
LITHIUM TETRAMETHYLPIPERIDIDE is used as a reagent for ortholithiation of arenes such as 1,3-bis(trifluoromethyl)benzene, 4,4-dimethyl-2-phenyl-2-oxazoline, 1,4-bis(trifluoromethyl)benzene, and 1,3-dimethoxybenzene. The strong basicity of LTMP allows for selective lithiation at the ortho position, which is crucial for the synthesis of various organic compounds and functional groups.
Used in Deprotonative Metalation with TMEDA:
LITHIUM TETRAMETHYLPIPERIDIDE is used in combination with the Lewis donor ligand, N,N,N′,N′-tetramethylethylenediamine (TMEDA), for deprotonative metalation of methoxy-substituted arenes. This application benefits from the strong basicity of LTMP and the coordinating ability of TMEDA, which together facilitate the metalation process and enable the synthesis of a range of aromatic compounds with high selectivity and reactivity.

Upstream product

• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 4111-54-0 lithium diisopropyl amide 
• 26954-24-5 3-(lithiomethyl)pyridine 
• 68695-92-1 (4,4'-Dimethyldiphenylmethyl)lithium 
• 557-20-0 diethylzinc 
• 591-51-5 phenyllithium 
• 109-72-8 n-butyllithium 
• 1078-58-6 diphenylzinc 

Downstream Products

• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 26954-24-5 3-(lithiomethyl)pyridine 
• 72821-01-3 N-trimethylsilylimidophosphenous acid 2,2,6,6-tetramethylpiperidine 
• 4039-32-1 lithium hexamethyldisilazane 
• 29779-72-4 1,2,2,6,6-Pentamethyl-1-cyclohexanol 
• 112269-97-3 2,2,6-trimethyl-2,3,4,5-tetrahydropyridine 
• 68695-92-1 (4,4'-Dimethyldiphenylmethyl)lithium 
• 127459-33-0 C₁₆H₁₄LiN₂ 
• 127459-26-1 2-((E)-1-Phenyl-propenylamino)-benzonitrile 
• 127459-26-1 2-((E)-1-Phenyl-propenylamino)-benzonitrile 
• 74601-40-4 phenyl(2,2,6,6-tetramethylpiperidin-1-yl)methanone 
• 7697-29-2 4-chloro-3-methylbenzoic acid 
• 58231-16-6 4-chloro-2-ethylbenzoic acid 
• 68837-59-2 4-bromo-2-methylbenzoic acid 

Relevant academic research and scientific papers

Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes

Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates. We have demonstrated the novel use of zincate base/nucleophile system for effective formation of key cyclohexyne intermediates and selective addition of various carbon and nitrogen nucleophiles. Importantly, leveraging the resulting organozincates enables the incorporation of a broad range of electrophilic partners to deliver structurally diverse cyclohexene motifs. The importance and utility of this method is also exemplified by the modularity of this approach and the ease in which even highly complex polycyclic scaffolds can be accessed in one step.

UROKINASE INHIBITORS

Disclosed are benzothiophene and thienothiophene derivatives useful for inhibiting urokinase activity.

BESTIMMUNG DER IONENPAAR-BASIZITAT VON LITHIUM- UND KALIUMAMIDEN

Ion pair basicities of lithio and potassio salts of some secondary amines were determined by equilibration with benzyl compounds.With these bases it is possible to span a range of about 19 pK-units from pK = 27 up to 46.The structural dependence of thermodynamic as well as kinetic basicity is discussed.Some new effective amide bases for preparative purposes are recommended.For the first time the pK-value of toluene has been determined by direct equilibration.It amounts to 40.7 in tetrahydrofuran.

LITHIUM DIALKYLAMIDES. 13C PARAMETERS AND SLOW PROTON TRANSFER

The changes in 13C chemical shifts for the structural change R2NH -> R2N-Li have been measured for a series of dialkylamines.These lithiation shifts are largest at the alpha carbon (3.7-9.7 ppm) and decrease in the order α > β > χ > δ.The rates of lithium-hydrogen interchange between R2NH and R'2N-Li have been determined.The activation energies are large (9 - 17 kcal/mole) and increase as the size of R or R' increases.The slow exchange permits the direct measurement of acidity differences between pairs of amines using 13C nmr.