Bulky 2,6-dibenzhydryl-4-methylaniline, I undergoes diazotization upon treatment with H₂SO₄/NaNO₂, which upon further reaction with KI affords 1-iodo-2,6-dibenzhydryl-4-methylbenzene, 1. Reaction of I with one equivalent of acetylacetone in ethanol under reflux condition affords mono-Schiff base, 4-(2,6-dibenzhydryl-4-methylphenylamino)pent-3-ene-2-one, 2. Similarly, I reacts with half equivalent of 2-hydroxy-5-methylisophthalaldehyde or one-third equivalent of 2,4,6-trihydroxybenzene-1,3,5- tricarbaldehyde in ethanol under reflux condition to afford bis-Schiff base, 2,6-bis(((2,6-dibenzhydryl-4-methylphenyl)imino)methyl)-4-methylphenol, 3 and tris-Schiff base, 2,4,6-tris(((2,6-dibenzhydryl-4- methylphenyl)amino)methylene)cyclohexane-1,3,5-trione, 4, respectively. Further, I upon reaction with triflic acid affords (2,6-dibenzhydryl-4-methylphenyl)ammonium triflate, 5 whereas upon reaction with HBr and HCl affords co-crystals I·HBr, 6 and I·HCl, 7. All the new products were isolated in moderate to good yield and characterized by spectroscopic (IR,ESI-mass,NMR,UV-Vis) and microanalytical (CHN) techniques, in additionto a single crystal X-ray diffraction study for 1, 2 and 4-7.
Volume 134, 2022
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