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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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Armstrong, D. R., Ball, S. C., Barr, D., Clegg, W., Linton, D. J., Kerr, L. C., Moncrieff, D., Raithby, P. R., Singer, R. J., Snaith, R., Stalke, D., Wheatley, A. E. H. and Wright, D. S., 2002. A solid state and theoretical study of the solvent effects controlling the mono- and di-lithiation of aromatic primary amines. Journal of the Chemical Society: Dalton Transactions

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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.

Details

Item Type Articles
CreatorsArmstrong, D. R., Ball, S. C., Barr, D., Clegg, W., Linton, D. J., Kerr, L. C., Moncrieff, D., Raithby, P. R., Singer, R. J., Snaith, R., Stalke, D., Wheatley, A. E. H. and Wright, D. S.
DOI10.1039/b107970k
Uncontrolled Keywordsreactivity, amide ladder structures, tetrahydrofuran, chemistry, ray crystal-structure, basis sets, cage molecule, ring-stacking, lithium anilide, tmeda = me2nch2ch2nme2
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code5171
Additional InformationID number: ISI:000176051000018

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