Synthesis of imidazoline derivatives via cycloaddition reaction of isocyanides based on chloroform to aldimines

AshEse Journal of Engineering                                                                   
Vol. 1(3), pp. 016-021, October, 2015
© 2015 AshEse Visionary Limited  
ISSN 2397-0677
 
Full Length Research Paper
Hanan El-Sharkawy Ali
Surfactant Laboratory, Petrochemical Department, Egyptian Petroleum Research Institute, Alzohor Zone, Nasr City, Cairo 00202, Egypt. E-mail address: This email address is being protected from spambots. You need JavaScript enabled to view it.
 
Received August, 2015; Accepted October, 2015
 
In an effort to develop new classes of NHC (N-heterocyclic carbenes) complexes, two imidazoline-anchored quat and bis-quat ligand systems have been synthesized. The process is superior owing to two approaches: (i) a new synthesized phase transfer catalyst, namely, 1,1’-benzene-1,4-diyldipyridinium dibromide (BDPDB) used to catalyze the phase-transfer hoffmann reaction of two structurally varied amines, dodecylamine and 1-amino-9, 10-anthraquinone. The reaction successfully gave the corresponding isocyanides that display the highest reactivity in reasonable to good yields. (ii) a cycloaddition-rearrangement reaction between imine and isocyanides based on chloroform gives easy access to a diverse range of highly substituted 4- and 2-imidazolines. Furthermore, imidazoline based bis-NHC (N-heterocyclic carbenes) precursors have been prepared and complexed to copper cation (4-L and 2-L, Figure 1). The molecular structures of the representative metal-NHC and metal-carbene bonds of these complexes have been elucidated and proved by elemental analyses, FT-IR, 1H & 13C NMR, and atomic adsorption spectroscopy. In contrast to the common assumption that NHCs are pure α-donors, the prepared complexes revealed a significant π-backbonding in electron-rich metal NHC complexes.
 
Keywords: PT Catalysis, imidazoline complexes, aldimines, isocyanides, imidazolines, 1, 1′-(ethane- 1, 2-diyl) dipyridinium bistribromide, MCRs, heterocyclic carbenes.
 

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