2,5-Diphenylfuran

synthetische2,5-Diphenylfuran Synthesis: Using the batch general procedure, commercially available trans,trans-1,4-diphenyl-1,3-butadiene (1) (412 mg, 2.00 mmol) and rose Bengal disodium salt (6 mg, 0.005 mmol) in 19:1 CHCl/MeOH (60 mL) provided the intermediate endoperoxide, 3,6-diphenyl-3,6-dihydro-1,2-dioxine (3), as a colorless solid after column chromatography (308 mg, 1.30 mmol, 65%); R_f = 0.15 (9/1 hexanes/ethyl acetate).1H NMR (CDCl, 500 MHz): δ 7.77 (d, 4H, J = 8.0 Hz), 7.43 (t, 4H, J = 7.5 Hz), 7.29 (t, 2H, J = 7.5 Hz), 6.75 (s, 2H).13C {1H} NMR (CDCl, 126 MHz): δ 137.7, 128.8, 128.7, 128.5, 127.5, 80.3.Using the general batch procedure and 3 (120 mg, 0.50 mmol), PPh (144 mg, 0.55 mmol), and CBr (182 mg, 0.55 mmol), 2,5-Diphenylfuran was obtained as a colorless solid after column chromatography (112 mg, 0.50 mmol, 99%); R_f = 0.40 (9/1 hexanes/ethyl acetate).1H NMR (CDCl, 500 MHz): δ 7.77 (d, 4H, J = 7.3 Hz), 7.43 (t, 4H, J = 7.5 Hz), 7.29 (t, 2H, J = 7.5 Hz), 6.76 (s, 2H).13C {1H} NMR (CDCl, 126 MHz): δ 153.4, 130.9, 128.8, 127.4, 123.8, 107.3.IR (ν_max, cm1): 2980, 1662, 1600, 1587, 1508, 1479, 1447, 1386.