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General Procedure for Fluorine Replacement A Schlenk flask was charged with the ethynyl derivative and anhyd THF. A solution of EtMgBr (1 M in THF) was then added dropwise and the mixture was stirred at 50°C for 2 h. The mixture was then added at 25°C via a cannula to a solution of 4a-c in anhyd THF. The mixture was stirred at 70°C for 16 h and the solvent was removed by rotary evaporation. The residue was treated with H 2O and extracted with CH2Cl2. The organic extracts were washed with H2O, and dried over MgSO4. The solvent was removed, and the residue was purified by chromatography. Compound 5a Prepared following general procedure from 4a (100 mg, 0.22 mmol, 1-ethynyltoluene (104 mg, 0.9 mmol, EtMgBr (0.41 mL, 0.41 mmol, 1 M in THF, THF (8 mL, Chromatography (silica gel, CH2Cl 2-cyclohexane, 30:70 to 50:50) gave 5a as a blue crystalline powder 60 mg, 42
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2: C, 88.68; H, 5.23; N, 4.40. Found: C, 88.40; H, 4.95; N, 4.18.
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34347331943
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2. CCDC 637684.
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2. CCDC 637684.
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25
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34347324711
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2. CCDC 623954.
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2. CCDC 623954.
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26
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34347360323
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Crystal Data for 6a at 293 K: [C49H33BN 2, 0.5 x (C6H12, C2H3N, M, 723.19, triclinic, space group P-1, a, 11.294 (4) Å, b, 13.299 (3) Å, c, 14.735 (4) Å, α, 101.78 (2)°, β, 110.03(2)°, γ, 102.17(2)°, V, 1938.4 (10) Å3, Z, 2, λ, 0.7107 Å, Dc= 1.239 g cm-3, μ, 0.071 mm-1, 10488 reflections collected with θ < 22.4°, 4585 unique, R(int, 0.0351, and 3135 observed reflections, I ≥ 2σ(I, 470 parameters, R1, 0.0649, wR2, 0.1879 refined on F 2. SQUEEZE macro within PLATON was used to take disordered solvent molecules (half a molecule of cyclohexane and half a molecule of MeCN in the asymmetric unit) into account during the structure refinement process. CCDC 62
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2. SQUEEZE macro within PLATON was used to take disordered solvent molecules (half a molecule of cyclohexane and half a molecule of MeCN in the asymmetric unit) into account during the structure refinement process. CCDC 623955.
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Olmsted, J. III J. Phvs. Chem. 1979, 83, 2581.
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