Is it possible to transform N,N-dimethylaniline (C8H11N) into N-methylaniline (C7H9N) by one or 2 steps?
The 2 compounds are bases. Which one is stronger & why?
Dr. Nizar,
This demethylation was reported, see
---Rosenau, Thomas et al. (2004) A General, Selective, High-Yield N-Demethylation Procedure for Tertiary Amines by Solid Reagents in a Convenient Column Chromatography-like Setup. Organic Letters, 6: 541-544.
---Shearer, Jason et al. (2003) Distinguishing Rate-Limiting Electron versus H-Atom Transfers in Cu2(O2)-Mediated Oxidative N-Dealkylations: Application of Inter- versus Intramolecular Kinetic Isotope Effects. J. Am. Chem. Soc. 125: 12670-12671.
---Liao, Qian and Xi, Chan-juan (2009) CuCl-catalyzed oxidative N-demethylation of arylamines with t-butyl hydroperoxide. Chemical Research in Chinese Universities, 25(6):861-865.
---Zhang, Jie et al.(2013) Iodide-Catalyzed Synthesis of N-Nitrosamines via C-N Cleavage of Nitromethane. J. Org. Chem.78: 11366-11372.
Good luck
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