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3,8-Bis-trimethylsilanylethynyl-[1,10]-phenanthroline

Department of Chemistry, Faculty of Sciences, Bu Ali Sina University, Hamedan, Iran. Code: 6517838683
Molbank 2005, 2005(3), M423; https://doi.org/10.3390/M423
Submission received: 13 June 2005 / Accepted: 8 August 2005 / Published: 1 September 2005
Molbank 2005 m423 i001
The experimental procedure follows a protocol developed by Sonogashira [1] and recently used for the preparation of macrocyclic phenanthrolines [2]. All reactions were carried out under the atmosphere of dry argon by using standard Schlenk tube techniques.
At first, a solution of 3,8-dibromo-[1,10]phenanthroline [3] (6.085 g, 18.0 mmol) and trimethylsilanylethyne (7.055 g, 72.0 mmol) in benzene (30 mL) and dry triethylamine (15 mL) was prepared. After addition of PdCl2(PPh3)2 (703 mg, 1.8 mmol) and CuI (686 mg, 3.6 mmol), the resulting mixture was kept at reflux for three days. After removal of the solvent, the black residue was dissolved in dichloromethane (150 mL), and washed with aqueous potassium cyanide (2%, 100 mL) and water (100 mL). The organic layer was dried over MgSO4 and then purified by column chromatography (SiO2, 1. CH2Cl2, 2. diethylether) to furnish 6.04 g (90%) of the title compound as colorless crystals.
Melting Point: ~150 °C.
IR (KBr, cm-1): 3056, 2956, 2154, 1589, 1494, 1420, 1248, 1100, 863, 838, 731, 656.
1H-NMR (200 MHz, CDCl3): δ= 0.1 (18H, 6CH3); 7.5 (2H, 5-H & 6-H); 8.2 (2H, 4-H & 7-H); 9.0 (2H, 2-H & 9-H).
Elemental Analysis: Calculated for C22H24N2Si2: C, 70.91%; H, 6.49%; N, 7.52%. Found: C, 70.7%; H, 6.4%; N, 7.8%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The author gratefully acknowledges financial support from the Bu Ali Sina University, Hamedan, Iran.

References

  1. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
  2. Schmittel, M.; Ammon, H. Synlett. 1999, 750.
  3. Tzalis, D.; Tor, Y.; Failla, S.; Siegel, J.S. Tetrahedron Lett. 1995, 36, 3489.

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MDPI and ACS Style

Habibi, D. 3,8-Bis-trimethylsilanylethynyl-[1,10]-phenanthroline. Molbank 2005, 2005, M423. https://doi.org/10.3390/M423

AMA Style

Habibi D. 3,8-Bis-trimethylsilanylethynyl-[1,10]-phenanthroline. Molbank. 2005; 2005(3):M423. https://doi.org/10.3390/M423

Chicago/Turabian Style

Habibi, Davood. 2005. "3,8-Bis-trimethylsilanylethynyl-[1,10]-phenanthroline" Molbank 2005, no. 3: M423. https://doi.org/10.3390/M423

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