Issue 12, 2002
From the journal:

Journal of the Chemical Society, Dalton Transactions

A solid state and theoretical study of the solvent effects controlling the mono- and di-lithiation of aromatic primary amines†

David R. Armstrong,*a   Sarah C. Ball,b   Donald Barr,c   William Clegg,d   David J. Linton,c   Lesley C. Kerr,c   David Moncrieff,e   Paul R. Raithby,f   Robert J. Singer,c   (the late) Ronald Snaith,c   Dietmar Stalke,g   Andrew E. H. Wheatley*c  and  Dominic S. Wrightc  

* Corresponding authors

a Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK

b Johnson Matthey, Blounts Court, Sonning Common, Reading, UK

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

d Department of Chemisty, University of Newcastle, Newcastle upon Tyne, UK

e School of Computational Science and Information Technology, Florida State University, Tallahassee, Florida, 32306, USA

f Department of Chemistry, University of Bath, Claverton Down, Bath, UK

g Institute for Inorganic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany

Abstract

Reaction of 1-naphthylamine, 4-tritylaniline or 4-methylaniline with two equivalents of BunLi in Et2O or thf affords rare geminal N,N-dilithiates of general formula (L)n·(Li2NAr)10 (L = Et2O, n = 6, Ar = 1-C10H71, C6H4-4-CPh32; L = thf, n = 10, Ar = C6H4-4-Me 3). X-Ray crystal structure analyses reveal that the core (Li14N10)6− frameworks consist of two fused rhombic dodecahedra. Ab initio M.O. calculations on the mono- and di-lithiation of 1-naphthylamine and 4-methylaniline suggest that the selectivity with which polymetallation occurs is solvent dependent and so help to rationalise the experimentally observed structures.

Graphical abstract: A solid state and theoretical study of the solvent effects controlling the mono- and di-lithiation of aromatic primary amines

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Article information

DOI
https://doi.org/10.1039/B107970K
Article type
Paper
Submitted
04 Sep 2001
Accepted
26 Apr 2002
First published
21 May 2002

J. Chem. Soc., Dalton Trans., 2002, 2505-2511

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A solid state and theoretical study of the solvent effects controlling the mono- and di-lithiation of aromatic primary amines

D. R. Armstrong, S. C. Ball, D. Barr, W. Clegg, D. J. Linton, L. C. Kerr, D. Moncrieff, P. R. Raithby, R. J. Singer, R. Snaith, D. Stalke, A. E. H. Wheatley and D. S. Wright, J. Chem. Soc., Dalton Trans., 2002, 2505 DOI: 10.1039/B107970K

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