2,2'-Bipyridine → HCID 102065214, compound

Participants

Reaction Conditions

Reaction Steps

Bis(1,5-cycloocatadiene)nickel(0) (0.193 g, 0.70 mmol), 1,5-cyclooctadiene (0.08 g, 0.09 mL, 0.70 mmol) and 2,2′-bipyridine (0.109 g, 0.70 mmol) were added to a flame-dried 100 mL Schlenk flask, dissolved in 9.4 mL of anhydrous N,N-dimethylformamide and stirred for 30 min at 65° C. in the absence of light. A solution of 2-bromo-4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine (0.25 g, 0.56 mmol) in 18.8 mL of anhydrous toluene at 65° C. was added slowly via a double-tipped needle and the resulting mixture was stirred for two days at 85° C. The reaction was quenched by adding 10% aqueous hydrochloric acid, extracted three times with CH2Cl2 and the organic phase was dried with MgSO4. After having removed the solvents in vacuo, the residue was subjected to column chromatography (silice, n-hexane/CH2Cl2 3:1) leading to triangulene dimer as a white crystalline solid (0.165 g, 80%).

Provenance & Evidence