Category: 4045-44-7

4045-44-7, 1,2,3,4,5-Pentamethylcyclopenta-1,3-diene is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a flame-dried, N2-purged three neck round-bottom flask, fit with a condenser, was added paraformaldehyde (580 mg) and dry THF (10.5 mL). The resulting suspension was heated at reflux under N2 for 2 h and then cooled to RT. To a separate flame-dried, N2-purged round bottom flask was added 1,2,3,4,5-pentamethylcyclopentadiene (0.6 mL, 3.83 mmol, 1.0 mol equiv.), tetrabutylammonium iodide (140 mg, 0.38 mmol, 0.1 mol equiv.), dry THF (8.0 mL), and a stir bar. The solution was cooled to 0 C and n-butyllithium (2.33 M, 4.6 mmol, 1.2 equiv) was added dropwise. A white precipitate immediately began to form. The suspension was stirred for 45 min at 0 C, and then the paraformaldehyde solution (230 mg, 7.66 mmol, 2.0 mol equiv.) was added and the resulting mixture was then stirred for 18 h, letting the ice bath expire. The solvent was then removed under reduced pressure and the solids were taken up in diethyl ether. This mixture was washed sequentially with 1.0 M HCl, sat. NaHCO3 aq., and H2O. The organic solution was dried over Na2SO4 and the solvent was removed under reduced pressure. The crude mixture was then purified by flash column chromatography to give a light yellow oil in 56% yield. 1H NMR (300 MHz, CDCl3) delta 3.50 (s, 2H), 1.77 (d, J = 18.8 Hz, 12H), 0.87 (s, 3H). 13C NMR (126 MHz, CDCl3) delta 138.0, 136.2, 65.3, 58.4, 16.8, 11.3, 9.7., 4045-44-7

As the paragraph descriping shows that 4045-44-7 is playing an increasingly important role.

Reference£º
Article; Peterson, Gregory I.; Church, Derek C.; Yakelis, Neal A.; Boydston, Andrew J.; Polymer; vol. 55; 23; (2014); p. 5980 – 5985;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

4045-44-7, 1,2,3,4,5-Pentamethylcyclopenta-1,3-diene is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

All glassware was dried in a 10000C oven, assembled and kept under a nitrogen purge throughout reaction. All solvents used were anhydrous. To a 100 mL, three-neck round bottom flask equipped with a reflux condenser, teflon stir bar, gas inlet, glass stopper and septum was added cobalt octacarbonyl (6.Og; 17.5 mmol) . The septum was replaced and assembled reaction flask purged an additional 5 minutes. Dichloromethane (50 mL) was then canulated into reaction flask and solution stirred for 5 minutes. To the reaction solution was added 1,2,3,4,5- pentamethylcyclopentadiene (3.1g; 22.7 mmol) and 1,3- cyclohexadiene ((2.5 mL; 26.2 mmol) . Septum was replaced with glass stopper and reaction mixture was stirred and brought to a gentle reflux which was maintained for one (1) hour. The reaction was cooled just until reflux stopped followed by a second addition of 1, 2, 3, 4, 5-pentamethylcyclopentadiene (2.4 g; 17.6 mmol) . Reflux was then continued for another two (2) hours. The reaction was then cooled and stirred overnight at room temperature.The condenser was and replaced with a gas inlet and the volatile material removed under reduced pressure maintaining a flask temperature of 15 – 20C. The dark red crude material (7.89g) was then transferred into a glovebox. The crude material was dissolved in hexanes (30 mL) and loaded into a column of alumina (Brockman I – neutral) previously rinsed with hexanes (200 mL) . The title compound was then eluted as an orange-brown band with hexanes (80OmL) . The solvent was removed under reduced pressure yielding deep red crystals of the title compound (6.09g; 70% based on Co2 (CO) 8) .The synthesis can be represented as follows: Co2(CO)8 + 2C5Me5H + C6H8 ? 2 [Co (omega5-C5Me5) (CO)2] + C6Hi0 + 4C0Analytical Characterization: 1H NMR spectrum was taken using a Bruker Avance 300 Spectrometer 1H NMR (C6D6) delta 1.6 (s, 5 CH3)

4045-44-7, As the paragraph descriping shows that 4045-44-7 is playing an increasingly important role.

Reference£º
Patent; PRAXAIR TECHNOLOGY, INC.; WO2008/124599; (2008); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4045-44-7,1,2,3,4,5-Pentamethylcyclopenta-1,3-diene,as a common compound, the synthetic route is as follows.

Under an argon atmosphere the excess of 1,2,3,4,5-pentamethylcyclopentadiene(19 mL, 0.167 mmol) was added to the suspensionof [(C8H14)2RhCl]2 (30 mg, 0.084 mmol) in C2H4Cl2 (1 ml).The reaction mixture was stirred overnight at room temperature.Then, the excess of NaHCO3 (84 mg, 1.00 mmol) was added and themixture was cooled to 0 C in an ice bath. The solution of bromine(135 mg, 43 mL, 0.84 mmol) in C2H4Cl2 (0.5 ml)was added dropwise.After the addition, the reaction mixture was stirred for another30 min at 0 C. The mixture was then opened to air and filtered, theprecipitate was washed with C2H4Cl2 (4 1 ml) and the combinedsolution was evaporated in vacuum. The precipitate (presumably[Cp*RhBr3]n) was washed with Et2O (32 ml) and dried in vacuum(20 mg, 50%). The obtained precipitate was suspended in hot C2H4Cl2 (3 ml)and ethylene was bubbled through until the complete dissolutionof the precipitate. The mixture was evaporated to dryness in vacuum.The residue was dissolved in CHCl3 (1 ml) and the product 3was precipitated by Et2O (5 ml) as red powder, which was dried invacuum (16 mg, 94%).1H NMR (400 MHz, CDCl3): delta 1.73 (s, 15H). 13C NMR (101 MHz,CDCl3): delta 94.98 (d, JRh-C 8.8 Hz), 10.15. Anal. Calc. forC10H15RhBr2: C 30.18, H 3.80; found: C 30.58, H 3.98., 4045-44-7

As the paragraph descriping shows that 4045-44-7 is playing an increasingly important role.

Reference£º
Article; Pototskiy, Roman A.; Lisov, Alexey A.; Nelyubina, Yulia V.; Perekalin, Dmitry S.; Journal of Organometallic Chemistry; vol. 862; (2018); p. 71 – 75;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI