Literature DB >> 11483070

Why is alkylation of an enolate accompanied by so much polyalkylation?

A Streitwieser1, Y J Kim, D Z Wang.   

Abstract

[reaction: see text] The lithium enolate 1-Li of 6-phenyl-alpha-tetralone forms a monomer-tetramer equilibrium in THF at 25 degrees C with K(1,4) = 4.7E+10 M(-3). The lithium enolate 2-Li, however, forms a monomer-dimer equilibrium with K(1,2) = 3800 M(-1). In both cases reaction with benzyl bromide is dominantly with the monomer. The results support an earlier conjecture of House that alkylation of an enolate is frequently accompanied by extensive polyalkylation because the less substituted enolates are more aggregated.

Entities:  

Year:  2001        PMID: 11483070     DOI: 10.1021/ol0162872

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


  9 in total

1.  Ion pair aggregates and reactions; experiment and theory.

Authors:  Andrew Streitwieser
Journal:  J Mol Model       Date:  2005-12-09       Impact factor: 1.810

2.  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

3.  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

Review 4.  Perspectives on computational organic chemistry.

Authors:  Andrew Streitwieser
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

5.  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

6.  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

7.  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

8.  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

9.  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

  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.