Literature DB >> 11843594

Equilibrium constants and alkylation kinetics of two lithium enolates/LiHMDS mixed aggregates in THF.

Yeong-Joon Kim1, Andrew Streitwieser.   

Abstract

[reaction: see text] Mixed aggregates between lithium enolates and lithium hexamethyldisilazide (LiHMDS) have been studied in THF using UV-vis spectroscopy. The equilibrium constants (K(agg)) between monomeric LiEn and monomeric LiHMDS are 760 and 560 M(-1) when LiEn are LiSIBP and LiBnPAT, respectively. The alkylation kinetics of the reactions with benzyl bromide were studied at 25 degrees C. The rate constants for the mixed aggregates, k(Mixed), are substantially smaller than those of the monomeric enolates.

Entities:  

Year:  2002        PMID： 11843594     DOI： 10.1021/ol017175d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  Lithium Hexamethyldisilazide-Mediated Enolization of Acylated Oxazolidinones: Solvent, Cosolvent, and Isotope Effects on Competing Monomer- and Dimer-Based Pathways.

Authors:  Gabriel J Reyes-Rodríguez; Russell F Algera; David B Collum
Journal:  J Am Chem Soc       Date:  2017-01-12       Impact factor: 15.419

2.  Enediolate-dilithium amide mixed aggregates in the enantioselective alkylation of arylacetic acids: structural studies and a stereochemical model.

Authors:  Yun Ma; Craig E Stivala; Ashley M Wright; Trevor Hayton; Jun Liang; Ivan Keresztes; Emil Lobkovsky; David B Collum; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2013-05-31       Impact factor: 15.419

3.  Structure determination using the method of continuous variation: lithium phenolates solvated by protic and dipolar aprotic ligands.

Authors:  Laura L Tomasevich; David B Collum
Journal:  J Org Chem       Date:  2013-07-15       Impact factor: 4.354

4.  Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates.

Authors:  Evan H Tallmadge; David B Collum
Journal:  J Am Chem Soc       Date:  2015-10-05       Impact factor: 15.419

5.  Azaaldol condensation of a lithium enolate solvated by N,N,N',N'-tetramethylethylenediamine: dimer-based 1,2-addition to imines.

Authors:  Timothy S De Vries; Angela M Bruneau; Lara R Liou; Hariharaputhiran Subramanian; David B Collum
Journal:  J Am Chem Soc       Date:  2013-03-04       Impact factor: 15.419

6.  Solution structures of lithium enolates, phenolates, carboxylates, and alkoxides in the presence of N,N,N',N'-tetramethylethylenediamine: a prevalence of cyclic dimers.

Authors:  Jocelyn M Gruver; Lara R Liou; Anne J McNeil; Antonio Ramirez; David B Collum
Journal:  J Org Chem       Date:  2008-09-10       Impact factor: 4.354

7.  Lithium phenolates solvated by tetrahydrofuran and 1,2-dimethoxyethane: structure determination using the method of continuous variation.

Authors:  Timothy S De Vries; Anandarup Goswami; Lara R Liou; Jocelyn M Gruver; Emily Jayne; David B Collum
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

8.  Structures of beta-amino ester enolates: new strategies using the method of continuous variation.

Authors:  Lara R Liou; Anne J McNeil; Gilman E S Toombes; David B Collum
Journal:  J Am Chem Soc       Date:  2008-12-24       Impact factor: 15.419

9.  Lithium enolates of simple ketones: structure determination using the method of continuous variation.

Authors:  Lara R Liou; Anne J McNeil; Antonio Ramirez; Gilman E S Toombes; Jocelyn M Gruver; David B Collum
Journal:  J Am Chem Soc       Date:  2008-03-13       Impact factor: 15.419

10.  Lithium Enolates Derived from Pyroglutaminol: Aggregation, Solvation, and Atropisomerism.

Authors:  Michael J Houghton; Naomi A Biok; Christopher J Huck; Russell F Algera; Ivan Keresztes; Stephen W Wright; David B Collum
Journal:  J Org Chem       Date:  2016-04-25       Impact factor: 4.354
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.