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

Lookup NU author(s): Emeritus Professor Bill CleggORCiD

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Abstract

Reaction of 1-naphthylamine, 4-tritylaniline or 4-methylaniline with two equivalents of (BuLi)-Li-n in Et2O or thf affords rare geminal N,N-dilithiates of general formula (L)(n).((LiNAr)-N-2)(10) (L = Et2O, n = 6, Ar = 1-C10H7 1, C6H4-4-CPh3 2; 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.

Publication metadata

Author(s): Armstrong DR, Ball SC, Barr D, Clegg W, Linton DJ, Kerr LC, Moncrieff D, Raithby PR, Singer RJ, Snaith R, Stalke D, Wheatley AEH, Wright DS

Publication type: Article

Publication status: Published

Journal: Journal of the Chemical Society: Dalton Transactions

Year: 2002

Issue: 12

Pages: 2505-2511

ISSN (print): 1472-7773

ISSN (electronic): 1364-5447

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b107970k

DOI: 10.1039/b107970k

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