A five fused ring non-benzenoid quinone containing a seven-membered ring: synthesis and properties of cyclohept[f,g]aceanthrylene-5,8-dione and 1,2-dihydrocyclohept[f,g]aceanthrylene-5,8-dione

Abstract

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1,1′-Biaceanthrylene and 2,2′-Biaceanthrylene: Models for Linking Larger Polycyclic Aromatic Hydrocarbons via Five-Membered Rings

“…This compound was subjected to homodimerization with Ni­(COD) 2 and 2,2′-bipyridine to give the outwardly projecting derivative 5 . To gain access to the inwardly projecting isomer 6 , previously described aceanthrylen-1­(2 H )-one 9 was converted into an enolate with lithium diisopropylamide , followed by quenching with triflic anhydride to give 10 in poor, but utilizable, yield. The homocoupling of 10 with Ni­(COD) 2 and 2,2′-bipyridine gave 6 in good yield.…”

1,1’-Biaceanthrylene and 2,2'-Biaceanthrylene: Models for Linking Larger Polycyclic Aromatic Hydrocarbons via Five-Membered Rings

“…13 Aceanthrylen-1(2H)-one (9). 15 In a 500 mL round bottom flask was combined anthracene (5.35 g, 30.0 mmol), 2-chloroacetyl chloride (2.39 mL, 30.0 mmol) and 200 mL dichloromethane in ice bath. After the solution was cooled to 0 ℃, aluminum chloride (8.00 g, 60.0 mmol) was added over a period of 45 min.…”

“…This compound was subjected to homodimerization with Ni(COD)2 and 2,2'-bipyridine to give the outwardly projecting derivative 5. To gain access to the inwardly projecting isomer 6, previously described aceanthrylen-1(2H)-one 9 15 was converted into an enolate with lithium diisopropylamide 16,17 followed by quenching with triflic anhydride to give 10 in poor, but utilizable, yield. The homocoupling of 10 with Ni(COD)2 and 2,2'-bipyridine gave 6 in good yield.…”

1,1’-Biaceanthrylene and 2,2'-Biaceanthrylene: Models for Linking Larger Polycyclic Aromatic Hydrocarbons via Five-Membered Rings

“…This compound was subjected to homodimerization with Ni(COD)2 and 2,2'-bipyridine to give the outwardly projecting derivative 5. To gain access to the inwardly projecting isomer 6, previously described aceanthrylen-1(2H)-one 9 15 A single-crystal X-ray structure of 5 was solved and can be found in Figure 2. The two chromophore segments, that are effectively projected away from each other, were found to be almost (Figure 3).…”