1367875-71-5Relevant academic research and scientific papers
Synthesis and characterization of (-)-menthyl containing N-alkyl cycloimmonium salts
Hettstedt, Christina,Betzl, Wolfgang,Karaghiosoff, Konstantin
, p. 377 - 382 (2012)
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. Copyright
