Citation: Xiangru Meng, Gang Li. Synthesis of Diacetylferrocene and Analysis of Photo-ligand Exchange Reaction Product between Diacetylferrocene and 1,10-Phenanthroline: A New and Interesting Comprehensive Chemistry Experiment[J]. University Chemistry, ;2021, 36(6): 200806. doi: 10.3866/PKU.DXHX202008065 shu

Synthesis of Diacetylferrocene and Analysis of Photo-ligand Exchange Reaction Product between Diacetylferrocene and 1,10-Phenanthroline: A New and Interesting Comprehensive Chemistry Experiment

Xiangru Meng ,
Gang Li ^,

Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, China

Corresponding author: Gang Li, gangli@zzu.edu.cn
Received Date: 27 August 2020

1,1-diacetylferrocene (DAF) was synthesized through Friedel-Crafts acylation reaction by using ferrocene and acetylchloride as starting materials. This process involves basic laboratory skills, such as low temperature control, anhydrous and anoxic operation, extraction, vacuum distillation and recrystallization. The photo-ligand exchange reaction between DAF and 1,10-phenanthroline (phen) was carried out under visible light irradiation due to the photosensitivity of DAF and the strong chelating ability of phen. Phen substituted acetyl cyclopentadiene ligand, and produced complex[Fe(phen)₃](C₅H₄COCH₃)₂·CH₃CN·2H₂O. The composition of the photoreaction product was determined by means of powder X-ray diffraction, elemental analysis, infrared spectrum and ¹H NMR spectra. This comprehensive chemistry experiment is appropriate in difficulty, and the testing methods are diversified, which enables junior or senior undergraduates to complete a basic scientific research training process independently on the basis of comprehensive laboratory (I) and basic inorganic, analytical and organic chemistry laboratories.
- 1,1-Diacetylferrocene,
- 1,10-Phenanthroline,
- Photo-ligand exchange reaction,
- Comprehensive chemistry experiment
References
1. [1]
  Kealy, T. J.; Pauson, P. L. Nature 1951, 168, 1039.
2. [2]
  Wilkinson, G.; Rosenblum, M.; Whiting, M. C.; Woodward, R. B. J. Am. Chem. Soc. 1952, 74 (8), 2125.
3. [3]
  Fisher, E. O.; Pfab, W. Z. Naturforsch. 1952, 7b, 377.
4. [4]
  Rahimi, M.; Chermette, H.; Jamehbozorgi, S.; Ghiasi, R.; Kalhor, M. P. Russ. J. Phys. Chem. 2019, A93 (9), 1747.
5. [5]
  Miller, J. S. Chem. Rev. 1988, 88 (1), 201.
6. [6]
  Foo, K.; Sella, E.; Thomé, I.; Eastgate, M. D.; Baran, P. S. J. Am. Chem. Soc. 2014, 136 (14), 5279.
7. [7]
8. [8]
  Roman, E.; Dabard, R.; Moinet, C.; Astruc, D. Tetrahedron Lett. 1979, 16, 1433.
9. [9]
  Astruc, D. Tetrahedron 1983, 39 (24), 4027.
10. [10]
  Sutherland, R. G.; Iobal, M.; Piórko, A. J. Organomet. Chem. 1986, 302 (3), 307.
11. [11]
  Nesmeyanov, A. N.; Vol'kenau, N. A.; Bolesova, I. N. Tetrahedron Lett. 1963, 94 (25), 1725.
12. [12]
  Astruc, D. Tetrahedron Lett. 1973, 4 (36), 3437.
13. [13]
  Che, D. J.; Li, G.; Du, B. S.; Zhang, Z.; Li, Y. H. Inorg. Chim. Acta 1997, 261 (2), 121.
14. [14]
15. [15]
  Xia, X.; Yu, H.; Wang, L.; Deng, Z.; Shea, K. J.; Abdina, Z. U. Eur. Polym. J. 2018, 100, 103.
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
  Okuyama, T.; Ikenouchi, Y.; Fueno, T. J. Am. Chem. Soc. 1978, 100 (19), 6162.
1. [1]
  Kealy, T. J.; Pauson, P. L. Nature 1951, 168, 1039.
2. [2]
  Wilkinson, G.; Rosenblum, M.; Whiting, M. C.; Woodward, R. B. J. Am. Chem. Soc. 1952, 74 (8), 2125.
3. [3]
  Fisher, E. O.; Pfab, W. Z. Naturforsch. 1952, 7b, 377.
4. [4]
  Rahimi, M.; Chermette, H.; Jamehbozorgi, S.; Ghiasi, R.; Kalhor, M. P. Russ. J. Phys. Chem. 2019, A93 (9), 1747.
5. [5]
  Miller, J. S. Chem. Rev. 1988, 88 (1), 201.
6. [6]
  Foo, K.; Sella, E.; Thomé, I.; Eastgate, M. D.; Baran, P. S. J. Am. Chem. Soc. 2014, 136 (14), 5279.
7. [7]
8. [8]
  Roman, E.; Dabard, R.; Moinet, C.; Astruc, D. Tetrahedron Lett. 1979, 16, 1433.
9. [9]
  Astruc, D. Tetrahedron 1983, 39 (24), 4027.
10. [10]
  Sutherland, R. G.; Iobal, M.; Piórko, A. J. Organomet. Chem. 1986, 302 (3), 307.
11. [11]
  Nesmeyanov, A. N.; Vol'kenau, N. A.; Bolesova, I. N. Tetrahedron Lett. 1963, 94 (25), 1725.
12. [12]
  Astruc, D. Tetrahedron Lett. 1973, 4 (36), 3437.
13. [13]
  Che, D. J.; Li, G.; Du, B. S.; Zhang, Z.; Li, Y. H. Inorg. Chim. Acta 1997, 261 (2), 121.
14. [14]
15. [15]
  Xia, X.; Yu, H.; Wang, L.; Deng, Z.; Shea, K. J.; Abdina, Z. U. Eur. Polym. J. 2018, 100, 103.
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
  Okuyama, T.; Ikenouchi, Y.; Fueno, T. J. Am. Chem. Soc. 1978, 100 (19), 6162.
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Synthesis of Diacetylferrocene and Analysis of Photo-ligand Exchange Reaction Product between Diacetylferrocene and 1,10-Phenanthroline: A New and Interesting Comprehensive Chemistry Experiment

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通讯作者: 陈斌, bchen63@163.com