Stability and decarbonylation of 1,3-dialkyl-2-formylimidazolium perchlorate in solution

Author:

Xin Hong-Xing1,Liu Qi1,Yan Hong1,Song Xiu-Qing1

Affiliation:

1. College of Life Science and Bio-engineering, Beijing University of Technology, Pingleyuan Street No. 100, Chaoyang District, Beijing 100124, China.

Abstract

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.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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