Monometallation of a di(aminoaryl) ether induces a Smiles rearrangement leading to a sodium aryloxide complex: The synthesis and crystal structure of [(MeOCH2CH2)(C6H4NHCH 2CH2OMe)NC6H4O·Na] 2

Ian Cragg-Hine; Matthew G. Davidson; Oldrich Kocian; Thomas Kottke; Francis S. Mair; Ronald Snaith; J. Fraser Stoddart

doi:10.1039/C39930001355

Monometallation of a di(aminoaryl) ether induces a Smiles rearrangement leading to a sodium aryloxide complex: The synthesis and crystal structure of [(MeOCH₂CH₂)(C₆H₄NHCH ₂CH₂OMe)NC₆H₄O·Na] ₂

Ian Cragg-Hine, Matthew G. Davidson^*, Oldrich Kocian, Thomas Kottke, Francis S. Mair, Ronald Snaith, J. Fraser Stoddart

^*Corresponding author for this work

Chemistry

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Abstract

The title compound was synthesised by 1: 1 reaction of sodium hydride with a di(aminoaryl) ether ligand in toluene-hexamethylphosphoramide (HMPA) solution; X-ray crystallography revealed that an in situ Smiles rearrangement of the ligand had taken place to give a dimeric aryloxide sodium complex, which is in stark contrast to previous results obtained by 2: 1 reaction of BuⁿLi with the ligand in the absence of HMPA.

Original language	English (US)
Pages (from-to)	1355-1357
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	17
DOIs	https://doi.org/10.1039/C39930001355
State	Published - Dec 1 1993

ASJC Scopus subject areas

Molecular Medicine

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Cragg-Hine, I., Davidson, M. G., Kocian, O., Kottke, T., Mair, F. S., Snaith, R., & Stoddart, J. F. (1993). Monometallation of a di(aminoaryl) ether induces a Smiles rearrangement leading to a sodium aryloxide complex: The synthesis and crystal structure of [(MeOCH₂CH₂)(C₆H₄NHCH ₂CH₂OMe)NC₆H₄O·Na] ₂. Journal of the Chemical Society, Chemical Communications, (17), 1355-1357. https://doi.org/10.1039/C39930001355

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title = "Monometallation of a di(aminoaryl) ether induces a Smiles rearrangement leading to a sodium aryloxide complex: The synthesis and crystal structure of [(MeOCH2CH2)(C6H4NHCH 2CH2OMe)NC6H4O·Na] 2",

abstract = "The title compound was synthesised by 1: 1 reaction of sodium hydride with a di(aminoaryl) ether ligand in toluene-hexamethylphosphoramide (HMPA) solution; X-ray crystallography revealed that an in situ Smiles rearrangement of the ligand had taken place to give a dimeric aryloxide sodium complex, which is in stark contrast to previous results obtained by 2: 1 reaction of BunLi with the ligand in the absence of HMPA.",

author = "Ian Cragg-Hine and Davidson, {Matthew G.} and Oldrich Kocian and Thomas Kottke and Mair, {Francis S.} and Ronald Snaith and Stoddart, {J. Fraser}",

year = "1993",

month = dec,

day = "1",

doi = "10.1039/C39930001355",

language = "English (US)",

pages = "1355--1357",

journal = "Journal of the Chemical Society D: Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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}

Cragg-Hine, I, Davidson, MG, Kocian, O, Kottke, T, Mair, FS, Snaith, R & Stoddart, JF 1993, 'Monometallation of a di(aminoaryl) ether induces a Smiles rearrangement leading to a sodium aryloxide complex: The synthesis and crystal structure of [(MeOCH₂CH₂)(C₆H₄NHCH ₂CH₂OMe)NC₆H₄O·Na] ₂', Journal of the Chemical Society, Chemical Communications, no. 17, pp. 1355-1357. https://doi.org/10.1039/C39930001355

Monometallation of a di(aminoaryl) ether induces a Smiles rearrangement leading to a sodium aryloxide complex : The synthesis and crystal structure of [(MeOCH₂CH₂)(C₆H₄NHCH ₂CH₂OMe)NC₆H₄O·Na] ₂. / Cragg-Hine, Ian; Davidson, Matthew G.; Kocian, Oldrich et al.

In: Journal of the Chemical Society, Chemical Communications, No. 17, 01.12.1993, p. 1355-1357.

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

TY - JOUR

T1 - Monometallation of a di(aminoaryl) ether induces a Smiles rearrangement leading to a sodium aryloxide complex

T2 - The synthesis and crystal structure of [(MeOCH2CH2)(C6H4NHCH 2CH2OMe)NC6H4O·Na] 2

AU - Cragg-Hine, Ian

AU - Davidson, Matthew G.

AU - Kocian, Oldrich

AU - Kottke, Thomas

AU - Mair, Francis S.

AU - Snaith, Ronald

AU - Stoddart, J. Fraser

PY - 1993/12/1

Y1 - 1993/12/1

N2 - The title compound was synthesised by 1: 1 reaction of sodium hydride with a di(aminoaryl) ether ligand in toluene-hexamethylphosphoramide (HMPA) solution; X-ray crystallography revealed that an in situ Smiles rearrangement of the ligand had taken place to give a dimeric aryloxide sodium complex, which is in stark contrast to previous results obtained by 2: 1 reaction of BunLi with the ligand in the absence of HMPA.

AB - The title compound was synthesised by 1: 1 reaction of sodium hydride with a di(aminoaryl) ether ligand in toluene-hexamethylphosphoramide (HMPA) solution; X-ray crystallography revealed that an in situ Smiles rearrangement of the ligand had taken place to give a dimeric aryloxide sodium complex, which is in stark contrast to previous results obtained by 2: 1 reaction of BunLi with the ligand in the absence of HMPA.

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Cragg-Hine I, Davidson MG, Kocian O, Kottke T, Mair FS, Snaith R et al. Monometallation of a di(aminoaryl) ether induces a Smiles rearrangement leading to a sodium aryloxide complex: The synthesis and crystal structure of [(MeOCH₂CH₂)(C₆H₄NHCH ₂CH₂OMe)NC₆H₄O·Na] ₂. Journal of the Chemical Society, Chemical Communications. 1993 Dec 1;(17):1355-1357. doi: 10.1039/C39930001355

Monometallation of a di(aminoaryl) ether induces a Smiles rearrangement leading to a sodium aryloxide complex: The synthesis and crystal structure of [(MeOCH₂CH₂)(C₆H₄NHCH ₂CH₂OMe)NC₆H₄O·Na] ₂

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