Issue 7, 2007
From the journal:

Chemical Communications

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†

Mark S. Betson,a   Ann Bracegirdle,a   Jonathan Clayden,*a   Madeleine Helliwell,a   Andrew Lund,a   Mark Pickworth,a   Timothy J. Snapea  and  Christopher P. Worralla  

* Corresponding authors

a School of Chemistry, University of Manchester, Oxford Road, Manchester, UK
E-mail: clayden@man.ac.uk
Fax: +44 (0)161 275 4939

Abstract

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.

Graphical abstract: 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

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Article information

DOI
https://doi.org/10.1039/B614618J
Article type
Communication
Submitted
09 Oct 2006
Accepted
23 Nov 2006
First published
18 Dec 2006

Chem. Commun., 2007, 754-756

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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

M. S. Betson, A. Bracegirdle, J. Clayden, M. Helliwell, A. Lund, M. Pickworth, T. J. Snape and C. P. Worrall, Chem. Commun., 2007, 754 DOI: 10.1039/B614618J

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