Mesitylene based tris-N-heterocyclic carbene: synthesis and characterisation

Sharma, Manjul and G, Prabusankar (2018) Mesitylene based tris-N-heterocyclic carbene: synthesis and characterisation. Masters thesis, Indian Institute of Technology Hyderabad.

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Abstract

In this current work we are focusing on mesitylene based tris N-heterocyclic carbenes (selenated), with the molecular formula C42H48N6Se3 4. Which contains 3 N-substituted benzimidazole rings and a mesitylene moiety. For this, mesitylene methyl bromide, C12H15Br3 1 has to be prepared as starting material and prepared by the literature method. N-isopropyl benzimidazole 2 was prepared by adding KOH, DMSO and benzimidazole and after that isopropyl bromide. After getting both mesitylene methyl bromide and N-isopropyl benzimidazole further the coupling reaction was carried out in dry Acetonitrile. As the coupled product C42H51N6Br3 2,4,6-N’-benzimidazolium (N-iPr)-mesitylene bromide 3 is formed, further selenation was done in methanol and extracted in DCM. Finally the selenated product C42H48N6Se3 2,4,6-N’-benzimidazole (N-iPr)-selone-mesitylene 4 was obtained. All the structure of compounds 1, 2, 3 and 4 were established by IR, 1H and 13C NMR spectroscopy.

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