Acenaphthenequinone → Bis(4-allyl-2,6-diisopropylphenylimino)acenaphthene

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Reaction Steps

A mixture of 1.00 g of acenaphthoquinone (5.5 mmol) and 4-allyl-2,6-diisopropylaniline (2.49 g, 11.1 mmol) in acetic acid (10 mL) was heated to reflux. After 1 h the mixture was cooled to room temperature, and the solid was filtered. The product was washed with acetic acid (5 mL), hexane (4×10 mL) and dried in vacuum, yielding 2.59 g as a yellow-golden solid (82%). 1H-NMR (400 MHz, CDCl3): δ 7.86 (d, 2H, Ho-Ace-C═N), 7.37 (t, 2H, Hm-Ace-C═N), 7.07 (s, 4H, H—Ar—N═C), 6.65 (d, 2H, Hp-Ace-C═N), 6.15 (m, 2H, CH═C), 5.15 (m, 4H, C═C—H), 3.50 (d, 4H, CH2—C═C), 3.00 (m, 4H, CH(Me)2),1.22 (d,12H, C(CH3)2), 0.96 (d, 12H, C(CH3)2). Anal. Calcd for C42H48N2: C, 86.86; H, 8.32; N, 4.82. Found: C, 87.75; H, 7.35; N, 4.82.

Provenance & Evidence