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

David R. Armstrong; Sarah C. Ball; Donald Barr; William Clegg; David J. Linton; Lesley C. Kerr; David Moncrieff; Paul R. Raithby; Robert J. Singer; Ronald Snaith; Dietmar Stalke; Andrew E. H. Wheatley; Dominic S. Wright

doi:10.1039/B107970K

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Journal of the Chemical Society, Dalton Transactions

Issue 12, 2002

The international journal for inorganic, organometallic and bioinorganic chemistry

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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 Ronald Snaith,^c Dietmar Stalke,^g Andrew E. H. Wheatley*^c and Dominic S. Wright^c

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

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

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

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

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

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

Institute for Inorganic Chemistry, University of Würzburg, Am Hubland, Germany

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

DOI: 10.1039/B107970K
Received 04 Sep 2001, Accepted 26 Apr 2002
First published online 21 May 2002

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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.

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

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