9-(2-nitrovinyl)anthracene

Synthesis

GENERAL METHOD: 9-Anthracenecarboxaldehyde (1; 2.06 g, 10 mmol) was dissolved in anhydrous dichloromethane (20 mL). To this solution nitromethane (559 μL, 10 mmol) and piperidine (202 μL, 2 mmol) were added sequentially. The reaction mixture was heated to reflux and maintained for 8 hours. After completion of the reaction, it was cooled to room temperature and a red solid precipitated. The solid product was collected by filtration and washed with hexane (20 mL) to afford the target compound 9-(2-nitrovinyl)anthracene (1.70 g, 68% yield) as a red solid. Compound Registry Number: 55446-60-1; Thin Layer Chromatography Rf value = 0.56 (Expanding Agent Ratio: Hexane:Ethyl Acetate = 80:20); 1H NMR (CDCl3, 300 MHz) δ = 7.49-7.65 (m, 5H, aromatic hydrogens and -CH=CHNO2), 8.07 (d, J=7.9 Hz, 2H, aromatic hydrogens), 8.20 (d, J=8.8 Hz, 2H, aromatic hydrogen), 8.56 (s, 1H, H-10), 9.03 (d, J=13.8 Hz, 1H, -CH=CHNO2). Ref: Becker, H.D.; Soerensen, H.; Sandros, K. J. Org. Chem. 1986, 51, 3223-3226.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 32, p. 4306 - 4308
[2] Doklady Chemistry, 1975, vol. 225, p. 681 - 684
[3] Dokl. Akad. Nauk SSSR Ser. Khim., 1975, vol. 225, # 6, p. 1323 - 1326
[4] Inorganica Chimica Acta, 2015, vol. 426, p. 119 - 125
[5] Synthetic Communications, 2017, vol. 47, # 6, p. 551 - 556