Strong nucleophilic organic phosphine compound for polar vinyl monomer polymerization, and preparation method and application thereof
A technology of vinyl monomers and strong nucleophilicity, applied in the fields of compounds of Group 5/15 elements of the periodic table, organic chemistry, chemical instruments and methods, etc., to achieve mild polymerization conditions, convenient operation, and easy modification of organic phosphine structures Effect
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Embodiment 1
[0034]
[0035] The synthesis of raw material functionalized bis-imidazole functionalized organic guanidine (BIG-1) can be found in the literature (Angew. Chem. Int. Ed., 2014, 53, 1435-1438). In the glove box, BIG-1 (0.48 mmol), diisopropylphosphine chloride (0.48 mmol) and tetrahydrofuran (3 mL) were added separately to a 50 mL Schlenk bottle equipped with a magnet. After the reaction was stirred at 25°C for 24 hours, THF was removed in vacuo, and the precipitated solid was washed with n-hexane (3×10 mL) to obtain the target product precursor salt intermediate BIG-1-HCl.
[0036] The intermediate BIG-1-HCl (0.45 mmol), potassium hydride (0.68 mmol), potassium tert-butoxide (0.045 mmol) and tetrahydrofuran (5 mL) were added to a 25 mL round bottom flask, respectively. After the reaction was stirred at 25°C for 2 hours, the solid was removed by suction filtration, and the solvent was removed in vacuo to obtain the target product BIG-1-P. The yield was 85%.
[0037] yell...
Embodiment 2
[0039]
[0040] In the glove box, BIG-2 (0.48 mmol), di-tert-butylphosphine chloride (0.48 mmol) and tetrahydrofuran (3 mL) were added separately to a 20 mL Schlenk bottle equipped with a magnet. After the reaction was stirred at 25°C for 24 hours, THF was removed in vacuo, and the precipitated solid was washed with n-hexane (3×10 mL) to obtain the target product precursor salt intermediate BIG-2-HCl.
[0041] Intermediate (0.45mmol), potassium hydride (0.68mmol )、 Potassium tert-butoxide (0.045 mmol) and tetrahydrofuran (5 mL) were added to a 25 mL round bottom flask. After the reaction was stirred at 25° C. for 2 hours, the solid was removed by suction filtration, and the solvent was removed in vacuo to obtain the target product BIG-2-P. The yield was 87%.
[0042] Dark red solid. 1 H NMR (400MHz, C 6 D. 6 )δ4.93(dt,J=13.9,6.9Hz,4H),1.68(s,12H),1.56(d,J=9.7Hz,18H),1.40(d,J=7.1Hz,25H). 13 C NMR (151MHz, C 6 D. 6 )δ164.49(d, J=12.8Hz), 150.52(s), 116.83(s), 47.00(...
Embodiment 3
[0044]
[0045] In the glove box, BIG-3 (0.48 mmol), dicyclohexylphosphine chloride (0.48 mmol) and tetrahydrofuran (3 mL) were added separately to a 20 mL Schlenk bottle equipped with a magnet. After the reaction was stirred at 25°C for 24 hours, THF was removed in vacuo, and the precipitated solid was washed with n-hexane (3×10 mL) to obtain the target product precursor salt intermediate BIG-3-HCl.
[0046] The intermediate (0.45 mmol), potassium hydride (0.68 mmol), potassium tert-butoxide (0.045 mmol) and tetrahydrofuran (5 mL) were added separately to a 25 mL round bottom flask. After the reaction was stirred at 25°C for 2 hours, the solid was removed by suction filtration, and the solvent was removed in vacuo to obtain the target product BIG-3-P. The yield was 65%.
[0047] yellow solid. 1 H NMR (400MHz, C 6 D. 6 )δ4.95 (dt, J=13.7, 6.7Hz, 4H), 2.31 (dd, J=40.0, 12.3Hz, 5H), 2.03–1.75 (m, 13H), 1.67 (d, J=4.8Hz, 12H ), 1.42(d, J=7.0Hz, 25H), 1.09(s, 2H). 13 C ...
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