Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines |
| |
Authors: | Adler Thomas Bonjoch Josep Clayden Jonathan Font-Bardía Mercè Pickworth Mark Solans Xavier Solé Daniel Vallverdú Lluís |
| |
Institution: | School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK. |
| |
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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|