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; Ann Bracegirdle; Jonathan Clayden; Madeleine Helliwell; Andrew Lund; Mark Pickworth; Timothy J Snape; Christopher P Worrall

doi:10.1039/b614618j

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

Chem Commun (Camb). 2007 Feb 21:(7):754-6. doi: 10.1039/b614618j. Epub 2006 Dec 18.

Authors

Mark S Betson¹, Ann Bracegirdle, Jonathan Clayden, Madeleine Helliwell, Andrew Lund, Mark Pickworth, Timothy J Snape, Christopher P Worrall

Affiliation

¹ School of Chemistry, University of Manchester, Oxford Road, Manchester, UKM13 9PL.

PMID: 17392973
DOI: 10.1039/b614618j

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ethers / chemistry
Hydrocarbons, Aromatic / chemical synthesis*
Hydrocarbons, Aromatic / chemistry
Molecular Conformation
Organic Chemicals / chemical synthesis
Organic Chemicals / chemistry
Urea / chemistry

Substances

Ethers
Hydrocarbons, Aromatic
Organic Chemicals
Urea