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)

Abstract The reaction of 4‐[(CH 2 O) 2 CH]C 6 H 4 Br ( 1 ) with n ‐BuLi, followed by addition of HgCl 2 to the in situ formed organolithium derivative, affords [4‐{(CH 2 O) 2 CH}C 6 H 4 ] 2 Hg ( 2 ). Deprotection of the formyl groups of 2 in presence of p ‐TsOH ( p ‐Ts = 4‐MeC 6 H 4 SO 3 ) leads to [4‐(O=CH)C 6 H 4 ] 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 CH 2 Cl 2 , affords the novel diorganomercury(II) compounds of type [( E )‐4‐(RN=C)C 6 H 4 ] 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‐{(CH 2 O) 2 CH}C 6 H 4 ] 2 ( 8 ) and [4‐(O=CH)C 6 H 4 ] 2 ( 9 ) in presence of catalytic amounts of palladium(II) acetate. Compounds 2 – 9 were characterized by multinuclear magnetic resonance (NMR) ( 1 H, 13 C{ 1 H}, and 199 Hg{ 1 H}, 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.