Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N'-diarylureas and diaryl ethers: advantages of a relay axis

Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N'-diarylureas and diaryl ethers: advantages of a relay axis

The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N'-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95 : 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is ins...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2007-01 (7), p.754-756
Hauptverfasser: Betson, Mark S, Bracegirdle, Ann, Clayden, Jonathan, Helliwell, Madeleine, Lund, Andrew, Pickworth, Mark, Snape, Timothy J, Worrall, Christopher P
Format: Artikel
Sprache:eng
Schlagworte:
Ethers - chemistry
Hydrocarbons, Aromatic - chemical synthesis
Hydrocarbons, Aromatic - chemistry
Molecular Conformation
Organic Chemicals - chemical synthesis
Organic Chemicals - chemistry
Urea - chemistry
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Zusammenfassung:The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N'-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95 : 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond.
ISSN:1359-7345
1364-548X
DOI:10.1039/b614618j