Self-assembly in the metallation of bis(aminoaryl) ethers

Oldrich Kocian; Neil Spencer; J. Fraser Stoddart; Ian Cragg-Hine; Matthew Davidson; Francis S. Mair; Paul Raithby; Ronald Snaith; Thomas Kottke; Ehmke Pohl

doi:10.1016/0040-4020(94)00917-J

Self-assembly in the metallation of bis(aminoaryl) ethers

Oldrich Kocian, Neil Spencer, J. Fraser Stoddart, Ian Cragg-Hine, Matthew Davidson, Francis S. Mair, Paul Raithby, Ronald Snaith, Thomas Kottke, Ehmke Pohl

Research output: Contribution to journal › Article › peer-review

Abstract

The dilithiation of 2,2′-bis(2-methoxyethylamino)diphenyl ether (4) and 2,2′-bis(N,N-dimethylethylenediamino)diphenyl ether (7) in the absence of any Lewis base donor resulted in the formation of dimeric complexes 8 and 9, respectively, containing the unprecedented Li₄O₂N₄ "adamantanoid" metal core as a consequence of the self-recognition and self-assembly involving the two metallated subunits. In contrast, on monometallation using particular conditions, e.g. sodium hydride in the presence of Lewis base donor, the same ligands undergo a Smiles-type rearrangement, providing the first example of such a reaction involving an amine and a deactivated aromatic system. The conditions needed to promote this rearrangement have been investigated.

Original language	English
Pages (from-to)	579-590
Number of pages	12
Journal	Tetrahedron
Volume	51
Issue number	2
DOIs	https://doi.org/10.1016/0040-4020(94)00917-J
Publication status	Published - 9 Jan 1995

Funding

Financial support of this research by SERC, Associated Octel Company Limited, the University of Birmingham, and Queens' College and St John's College, Cambridge, is gratefully acknowledged.

Funders	Funder number
Associated Octel Co. Ltd.
University of Cambridge
Connecticut State Emergency Response Commission
University of Birmingham

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4020(94)00917-J

Cite this

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title = "Self-assembly in the metallation of bis(aminoaryl) ethers",

abstract = "The dilithiation of 2,2′-bis(2-methoxyethylamino)diphenyl ether (4) and 2,2′-bis(N,N-dimethylethylenediamino)diphenyl ether (7) in the absence of any Lewis base donor resulted in the formation of dimeric complexes 8 and 9, respectively, containing the unprecedented Li4O2N4 {"}adamantanoid{"} metal core as a consequence of the self-recognition and self-assembly involving the two metallated subunits. In contrast, on monometallation using particular conditions, e.g. sodium hydride in the presence of Lewis base donor, the same ligands undergo a Smiles-type rearrangement, providing the first example of such a reaction involving an amine and a deactivated aromatic system. The conditions needed to promote this rearrangement have been investigated.",

author = "Oldrich Kocian and Neil Spencer and \{Fraser Stoddart\}, J. and Ian Cragg-Hine and Matthew Davidson and Mair, \{Francis S.\} and Paul Raithby and Ronald Snaith and Thomas Kottke and Ehmke Pohl",

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T1 - Self-assembly in the metallation of bis(aminoaryl) ethers

AU - Kocian, Oldrich

AU - Spencer, Neil

AU - Fraser Stoddart, J.

AU - Cragg-Hine, Ian

AU - Davidson, Matthew

AU - Mair, Francis S.

AU - Raithby, Paul

AU - Snaith, Ronald

AU - Kottke, Thomas

AU - Pohl, Ehmke

PY - 1995/1/9

Y1 - 1995/1/9

N2 - The dilithiation of 2,2′-bis(2-methoxyethylamino)diphenyl ether (4) and 2,2′-bis(N,N-dimethylethylenediamino)diphenyl ether (7) in the absence of any Lewis base donor resulted in the formation of dimeric complexes 8 and 9, respectively, containing the unprecedented Li4O2N4 "adamantanoid" metal core as a consequence of the self-recognition and self-assembly involving the two metallated subunits. In contrast, on monometallation using particular conditions, e.g. sodium hydride in the presence of Lewis base donor, the same ligands undergo a Smiles-type rearrangement, providing the first example of such a reaction involving an amine and a deactivated aromatic system. The conditions needed to promote this rearrangement have been investigated.

AB - The dilithiation of 2,2′-bis(2-methoxyethylamino)diphenyl ether (4) and 2,2′-bis(N,N-dimethylethylenediamino)diphenyl ether (7) in the absence of any Lewis base donor resulted in the formation of dimeric complexes 8 and 9, respectively, containing the unprecedented Li4O2N4 "adamantanoid" metal core as a consequence of the self-recognition and self-assembly involving the two metallated subunits. In contrast, on monometallation using particular conditions, e.g. sodium hydride in the presence of Lewis base donor, the same ligands undergo a Smiles-type rearrangement, providing the first example of such a reaction involving an amine and a deactivated aromatic system. The conditions needed to promote this rearrangement have been investigated.

UR - https://www.scopus.com/pages/publications/0028931905

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EP - 590

JO - Tetrahedron

JF - Tetrahedron

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ER -

Self-assembly in the metallation of bis(aminoaryl) ethers

Abstract

Funding

ASJC Scopus subject areas

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