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Issue 12, 2002
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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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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


Submitted
04 Sep 2001
Accepted
26 Apr 2002
First published
21 May 2002

J. Chem. Soc., Dalton Trans., 2002, 2505-2511
Article type
Paper

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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