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

Thomas Adler, Josep Bonjoch, Jonathan Clayden*, Mercè Font-Bardía, Mark Pickworth, Xavier Solans, Daniel Solé, Lluís Vallverdú

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

57 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3173-3183
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume3
Issue number17
Early online date26 Jul 2005
DOIs
Publication statusPublished - 7 Sep 2005

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