Stability and decarbonylation of 1,3-dialkyl-2-formylimidazolium perchlorate in solution
2013 ◽
Vol 91
(6)
◽
pp. 442-447
◽
The stability of 1,3-dialkyl-2-formylimidazolium perchlorate 1 in solution was studied in detail and found to be related to its structure and the solvent character and temperature. 1 was stable in common solvents at room temperature and unstable in protic solvents under reflux. In protic solvents, such as H2O, MeOH, EtOH, and AcOH, 1 decarbonylated into 1,3-dialkylimidazole perchlorates 2, which was confirmed by 1H NMR, 13C NMR, HRMS, and X-ray spectroscopy. The decarbonylation of 1 was proposed to occur via its hemiacetal formed by the addition of solvents based on the tracking NMR spectra of 1 in deuterated reagents.
1992 ◽
Vol 47
(12)
◽
pp. 1725-1735
◽