Synthesis and characterization of [4-{(CH2O)2CH}C6H4]2Hg, [4-(O=CH)C6H4]2Hg and [(E)-4-(RN=CH)C6H4]2Hg (R=2′-py, 4′-py, 2′-pyCH2, 4′-pyCH2)

The reaction of 4-[(CH2O)(2)CH]C6H4Br (1) with n-BuLi, followed by addition of HgCl2 to the in situ formed organolithium derivative, affords [4-{(CH2O)(2)CH}C6H4](2)Hg (2). Deprotection of the formyl groups of 2 in presence of p-TsOH (p-Ts = 4-MeC6H4SO3) leads to [4-(O=CH)C6H4](2)Hg (3). Condensation reactions of 3 with 2-aminopyridine (2-pyNH(2)), 4-aminopyridine (4-pyNH(2)), 2-aminomethylpyridine (2-pyCH(2)NH(2)), and 4-aminomethylpyridine (4-pyCH(2)NH(2)), in CH2Cl2, affords the novel diorganomercury(II) compounds of type [(E)-4-(RN=C)C6H4](2)Hg [R = 2 '-py (4), 4 '-py (5), 2'-pyCH2- (6), 4 '-pyCH(2) (7)]. Compounds 2 and 3 were useful precursors for the preparation of the corresponding homocoupling products [4-{(CH2O)(2)CH}C6H4](2) (8) and [4-(O=CH)C6H4](2) (9) in presence of catalytic amounts of palladium(II) acetate. Compounds 2-9 were characterized by multinuclear magnetic resonance (NMR) (H-1, C-13{H-1}, and Hg-199{H-1}, when appropriate) and infrared (IR) spectroscopy and by mass spectrometry. The molecular structures of 3, 5, 6, 8, and 9 were determined by single-crystal X-ray diffraction.

Automated summary

In this study, novel organomercury(II) compounds were synthesized through a series of reactions, with the key step being the synthesis of ethanal groups with different functionalities. The molecular structures of some compounds were determined by single-crystal X-ray diffraction.