Butanedione → 2,3-Bis(2,5-bis(4-tert-butylphenyl)-pyrrol-1-ylimino)-butane

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Reaction Conditions

Reaction Steps

A solution of 2,5-bis-(4-tert-butyl-phenyl)-pyrrol-1-ylamine (174 mg, 0.502 mmol) in toluene (4.5 mL) was treated with butanedione (19.7 μL, 0.225 mmol) and p-toluene sulfonic acid (5.2 mg). The resulting solution was heated to 80° C. in an oil bath under Ar overnight. The solution was cooled to rt and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 33% CH2Cl2/heptane) to afford 2,3-bis(2,5-bis(4-tert-butylphenyl)-pyrrol-1-ylimino)-butane (121 mg, 72%): 1H NMR (CDCl3, chemical shifts in ppm relative to TMS): 1.33 (s, 36H), 1.69 (s, 6H), 6.39 (s, 4H), 7.33-7.39 (m, 16H).

Provenance & Evidence