Research article summary (published 31 Jan 2007):

n-Butyllithium/N,N,N',N'-tetramethylethylenediamine-mediated ortholithiations of aryl oxazolines: substrate-dependent mechanisms.

Full Abstract

n-Butyllithium/N,N,N',N'-tetramethylethylenediamine-mediated ortholithiations of aryloxazolines are described. Methyl substituents on the aryloxazoline and substituents at the meta position of the arenes (methoxy, oxazolinyl, and fluoro) influence the rates and the mechanisms. Monomer- and dimer-based reactions are implicated. Density functional calculations probe details of the mechanism and suggest the origins of cooperative effects in meta-substituted aryl oxazolines.

Author information

Author/s: Chadwick, Scott T (ST); Ramirez, Antonio (A); Gupta, Lekha (L); Collum, David B (DB);

Affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.

Journal and publication information

Publication Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.

Journal: Journal of the American Chemical Society (J Am Chem Soc), published in United States. (Language: eng)

Reference: 2007-Feb; vol 129 (issue 8) : pp 2259-68

Dates: Created 2007/02/21; Completed 2007/05/15;

PMID: 17269777, status: MEDLINE (last retrieval date: 2/18/2009, IMS Date: )

Sourced from the National Library of Medicine. Abstract text and other information may be subject to copyright.

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MeSH headings (categories)

This article was linked to the MESH Headings shown below.

Ethylenediamines - chemistry Lithium - chemistry Models, Chemical Models, Molecular Molecular Structure

Molecular Structure Organometallic Compounds - chemical synthesis; chemistry Oxazoles - chemistry Quantum Theory Stereoisomerism

Associated Chemicals: Ethylenediamines (0) ; Organometallic Compounds (0) ; Oxazoles (0) ; N,N,N',N'-tetramethylethylenediamine (110-18-9) ; Lithium (7439-93-2)

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