Compound 1b

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InChIKey YGTURXBNAHQDHD-UHFFFAOYSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

To a mixture of CuCl (13 mg, 0.13 mmol) in CH₂Cl₂ (20 mL) was added TMEDA (46 mg, 59 µL, 0.40 mmol). O₂ was bubbled through the solution for 5 min, a solution of 2c (86 mg, 0.13 mmol) in CH₂Cl₂ (5 mL) was then added and the reaction mixture stirred for 20 min. The reaction was plugged through silica gel with CH₂Cl₂ and the solvent removed in vacuo to yield 1b (57 mg, 66%) as a yellow solid: Mp 270 °C (decomp); R_f=0.25 (hexanes); IR (microscope) 3069 (w), 2960, 2903, 2866, 2201, 2178, 1592 cm⁻¹; UV-Vis (hexanes) λ_max (ϵ) 310 (412000), 292 (286000), 276 (144000), 262 (66000), 250 (38000), 208 (153000) nm; UV-Vis (CH₂Cl₂) λ_max (ϵ) 315 (247000), 295 (193000), 279 (110000) nm; UV-Vis (THF) λ_max (ϵ) 315 (257000), 296 (198000) nm; ¹H NMR (500 MHz, CDCl₃): δ 7.25 (t, J=2 Hz, 6H), 6.88 (d, J=2 Hz, 12H), 1.18 (s, 108H); ¹³C NMR (100 MHz, CDCl₃): δ 150.2, 143.3, 123.7, 120.4, 86.27, 68.78, 62.96, 62.90, 62.75, 62.42, 57.29, 34.8, 31.4; MALDI HRMS m/z calcd. for C₉₈H₁₂₆ (M⁺) 1302.9854, found 1302.9843; Anal. calcd. for C₉₈H₁₂₆: C, 90.26; H, 9.74. Found: C, 89.98; H, 9.79; DSC: decomposition, 300 °C (onset), 323 °C (peak) and 347 (peak).