Issue 14, 2003
From the journal:

Chemical Communications

Variations in the solid-state, solution and theoretical structures of a laterally deprotonated aromatic tertiary amide†

David R. Armstrong,a   Jonathan Clayden,*b   Robert Haigh,c   David J. Linton,c   Paul Schoolerc  and  Andrew E. H. Wheatley*c  

* Corresponding authors

a Department of Pure and Applied Chemistry, University of Strathclyde, Cathedral Street, Strathclyde, UK

b Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK

c Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK

Abstract

Reaction of 2-ethyl-N,N-diisopropyl-1-naphthamide 3 with ButLi in tetrahydrofuran (thf) affords a laterally metallated derivative which exists as a tris(thf) solvated monomer with no Li–C interaction and an sp2 hybridised carbanionic centre in the solid-state; NMR spectroscopy suggests that this structure is viable in solution but that Li–C bonded atropisomers are also possible and calculations corroborate these data.

Graphical abstract: Variations in the solid-state, solution and theoretical structures of a laterally deprotonated aromatic tertiary amide

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Article information

DOI
https://doi.org/10.1039/B302283H
Article type
Communication
Submitted
27 Feb 2003
Accepted
22 May 2003
First published
12 Jun 2003

Chem. Commun., 2003, 1694-1695

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Variations in the solid-state, solution and theoretical structures of a laterally deprotonated aromatic tertiary amide

D. R. Armstrong, J. Clayden, R. Haigh, D. J. Linton, P. Schooler and A. E. H. Wheatley, Chem. Commun., 2003, 1694 DOI: 10.1039/B302283H

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