Dedicated to Professor Wolfgang Beck on the Occasion of His 80th Birthday
Synthesis and Characterization of (–)-Menthyl Containing N-Alkyl Cycloimmonium Salts †
Article first published online: 23 DEC 2011
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Zeitschrift für anorganische und allgemeine Chemie
Volume 638, Issue 2, pages 377–382, February 2012
How to Cite
Hettstedt, C., Betzl, W. and Karaghiosoff, K. (2012), Synthesis and Characterization of (–)-Menthyl Containing N-Alkyl Cycloimmonium Salts . Z. anorg. allg. Chem., 638: 377–382. doi: 10.1002/zaac.201100451
Supporting Information for this article is available on the WWW under http://dx.doi.org/10.1002/zaac.201100451 or from the author.
- Issue published online: 16 FEB 2012
- Article first published online: 23 DEC 2011
- Manuscript Accepted: 23 DEC 2011
- Manuscript Received: 12 OCT 2011
- Department of Chemistry, Ludwig-Maximilian University of Munich
- N-Alkyl cycloimmonium salts; Aminothiazole; α-Bromoacetyl (–)-menthyl ester; Crystal structure; N–H···Br– hydrogen bonds
The reaction of 4-phenyl-2-aminothiazole or 2-amino pyridine with α-bromo acetic (–)-menthyl ester (2c) yields new N-alkyl cycloimmonium bromides (1c, 3) with the chiral (–)-menthyl substituent, which were isolated and fully characterized by 1H and 13C NMR spectroscopy for the first time. In addition, starting from 4-phenyl-2-aminothiazole, two further N-alkyl cycloimmonium bromides (1a, 1b) were prepared. The molecular and crystal structures of all three thiazole derived N-alkyl cycloimmonium bromides (1a–c) were determined by single-crystal X-ray diffraction. In all cases the crystal structures are dominated by N–H···Br hydrogen bonds, which results in the formation of an extensive hydrogen bonded network in the crystal. Interestingly, in all structures S···Br– distances shorter than the sum of the van der Waals radii are observed.