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Issue 17, 2005
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Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines

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Abstract

N-Acylated 2-substituted anilines undergo slow Ar–N bond rotation, allowing in some cases isolation of enantiomeric or diastereoisomeric atropisomers and in others the determination of the rate of Ar–N bond rotation by NMR. 2-Iodoanilides bearing a branched N-substituent demonstrate sufficient enantiomeric stability to be resolvable, either by HPLC or by formation of diastereoisomeric lactanilide derivatives. For the first time, the rates of Ar–N rotation in 2-substituted N,N′-diarylureas have been established: they mainly fall in the region of 50–70 kJ mol−1 with a relatively weak dependence on substituent size.

Graphical abstract: Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines

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Publication details

The article was received on 23 May 2005, accepted on 29 Jun 2005 and first published on 26 Jul 2005


Article type: Paper
DOI: 10.1039/B507202F
Citation: Org. Biomol. Chem., 2005,3, 3173-3183
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    Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines

    T. Adler, J. Bonjoch, J. Clayden, M. Font-Bardía, M. Pickworth, X. Solans, D. Solé and L. Vallverdú, Org. Biomol. Chem., 2005, 3, 3173
    DOI: 10.1039/B507202F

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