Lithium Diisopropylamide-Mediated Ortholithiations: Lithium Chloride Catalysis
نویسندگان
چکیده
منابع مشابه
Lithium diisopropylamide-mediated ortholithiations: lithium chloride catalysis.
Ortholithiations of a range of arenes mediated by lithium diisopropylamide (LDA) in THF at -78 degrees C reveal substantial accelerations by as little as 0.5 mol % of LiCl (relative to LDA). Substrate dependencies suggest a specific range of reactivity within which the LiCl catalysis is optimal. Standard protocols with unpurified commercial samples of n-butyllithium to prepare LDA or commercial...
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The effects of lithium, an inhibitor of the recycling of inositol in the phosphatidylinositol cycle, on rabbit blastocyst growth and metabolism of phosphoinositides were investigated. Day 2 rabbit morulae were first cultured for 2 days in basic culture medium and then transferred to medium containing myo-[2H]inositol for culture for a further 3 days. At the end of culture, the resulting blastoc...
متن کاملLithium diisopropylamide: oligomer structures at low ligand concentrations.
One- and two-dimensional (6)Li and (15)N NMR spectroscopic studies of lithium diisopropylamide (LDA) solvated by substoichiometric concentrations of oxetane, THF, Et(2)O, and diisopropylamine are described. Partially solvated dimers and trimers are identified. Possible benefits of carrying out organolithium chemistry at low ligand concentrations are discussed.
متن کاملLithium diisopropylamide: solution kinetics and implications for organic synthesis.
Lithium diisopropylamide (LDA) is a prominent reagent used in organic synthesis. In this Review, rate studies of LDA-mediated reactions are placed in the broader context of organic synthesis in three distinct segments. The first section provides a tutorial on solution kinetics, emphasizing the characteristic rate behavior caused by dominant solvation and aggregation effects. The second section ...
متن کاملLithium diisopropylamide solvated by hexamethylphosphoramide: substrate-dependent mechanisms for dehydrobrominations.
Lithium diisopropylamide-mediated dehydrobrominations of exo-2-bromonorbornane, 1-bromocyclooctene, and cis-4-bromo-tert-butylcyclohexane were studied in THF solutions and THF solutions with added hexamethylphosphoramide (HMPA). Rate studies reveal a diverse array of mechanisms based on mono-, di-, and trisolvated monomers as well as triple ions. The results are contrasted with analogous elimin...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2009
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo802713y