Synthesis and Characterizarion of Copper (II) and Copper (III) Complexes of Pyrrole-Appended Oxacarbaporphyrin

Rajeev Kumar; Sivadhar Sharma

doi:10.5958/2231-3915.2020.00024.3

International Journal of Technology

ISSN

2231-3915 (Online)
2231-3907 (Print)

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Synthesis and Characterizarion of Copper (II) and Copper (III) Complexes of Pyrrole-Appended Oxacarbaporphyrin

Author(s): Rajeev Kumar, Sivadhar Sharma

Email(s): Email ID Not Available

DOI: 10.5958/2231-3915.2020.00024.3

Address: Rajeev Kumar*, Sivadhar Sharma
Department of Chemistry, Magadh University, Bodhgaya - 824234. *Corresponding Author

Published In: Volume - 10, Issue - 2, Year - 2020

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ABSTRACT:
The reaction of an O-confused porphyrin with a pendant pyrrole 4 and copper (II) acetate yields an organocopper- (III) diamagnetic complex 4-Cu (III) substituted at the C (3) position by the pyrrole and H. The transformation of 4-Cu (III), performed in aerobic conditions, gave a rare copper(II) organometallic compound 6-Cu(II). In the course of this process, the tetrahedral-trigonal rearrangement originated at the C (3) atom but effects the whole structure. The electron paramagnetic resonance spectroscopic features correspond to a copper (II) oxidation state. A crystallographic analysis of 6-Cu (II) confirmed the formation of a direct metal-C bond [Cu(II)-C 1.939(4) Å]. It was found that the Cu (II) complex of O-confused oxaporphyrin is sensitive to oxidative conditions. The degradation of 6-Cu(II) to yield copper(II) tripyrrinone complexes has been observed, which was considered as a peculiar case of dioxygen activation in a porphyrin-like environment. This process is accompanied by regioselective oxygenation at the inner C to form the 2-oxa-3-(2¢-pyrrolyl)-21-hydroxy carbaporphyrinato copper (II) complex ((pyrr)OCPO)CuII (8). The reaction of 6-Cu (II) with hydrogen peroxide, performed under heterophasic conditions, resulted in quantitative regioselective hydroxylation centered at the internal C (21) atom, also producing 8. Treatment of 8 with acid results in demetalation to form the nonaromatic 21-hydroxy O-confused porphyrin derivative ((pyrr) OCPOH)H (9).

Keywords:

degradation heterophasic conditions.

Cite this article:
Rajeev Kumar, Sivadhar Sharma. Synthesis and Characterizarion of Copper (II) and Copper (III) Complexes of Pyrrole-Appended Oxacarbaporphyrin. Int. J. Tech. 2020; 10(2):129-137. doi: 10.5958/2231-3915.2020.00024.3

Cite(Electronic):
Rajeev Kumar, Sivadhar Sharma. Synthesis and Characterizarion of Copper (II) and Copper (III) Complexes of Pyrrole-Appended Oxacarbaporphyrin. Int. J. Tech. 2020; 10(2):129-137. doi: 10.5958/2231-3915.2020.00024.3 Available on: https://ijtonline.com/AbstractView.aspx?PID=2020-10-2-3

REFERENCES:
1.   Chmielewski, P. J.; Latos-Grazù yn´ski, L.; Rachlewicz, K.; Głowiak, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 779.
2.   Furuta, H.; Asano, T.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 767.
3.   Pawlicki, M.; Latos-Grazù yn´ski, L. Chem. Rec. 2006, 6, 64.
4.   Furuta, H.; Maeda, H.; Osuka, A. Chem. Commun. 2002, 1795.
5.   Sprutta, N.; Latos-Grazù yn´ski, L. Tetrahedron Lett. 1999, 40, 8457.
6.   Chmielewski, M. J.; Pawlicki, M.; Sprutta, N.; Szterenberg, L.; Latos- Grazù yn´ski, L. Inorg. Chem. 2006, 45, 8664.
7.   Szterenberg, L.; Sprutta, N.; Latos-Grazù yn´ski, L. J. Inclusion Phenom. 2001, 41, 209.
8.   Pawlicki, M.; Latos-Grazù yn´ski, L. J. Org. Chem. 2005, 70, 9123.
9.   Pawlicki, M.; Latos-Grazù yn´ski, L. Chem.sEur. J. 2003, 9, 4650.
10.   Latos-Grazù yn´ski, L. Core-Modified Heteroanalogues of Porphyrins and Metalloporphyrins. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000; Vol. 2, Chapter 14, pp 361-416.
11.   Harvey, J. D.; Ziegler, C. J. Coord. Chem. ReV. 2003, 247, 1.
12.   Srinivasan, A.; Furuta, H. Acc. Chem. Res. 2005, 38, 10.
13.   Chmielewski, P. J.; Latos-Grazù yn´ski, L. Coord. Chem. ReV. 2005, 249, 2510.
14.   Harvey, J. D.; Ziegler, C. J. J. Inorg. Biochem. 2006, 100, 869.
15.   Maeda, H.; Furuta, H. Pure Appl. Chem. 2006, 78, 29.
16.   Chmielewski, P. J.; Latos-Grazù yn´ski, L.; Głowiak, T. J. Am. Chem. Soc. 1996, 118, 5690.
17.   Furuta, H.; Morimoto, T.; Osuka, A. Inorg. Chem. 2004, 43, 1618.
18.   Chmielewski, P. J.; Latos-Grazù yn´ski, L. Inorg. Chem. 1997, 36, 840.
19.   Furuta, H.; Ogawa, T.; Uwatoko, Y.; Araki, K. Inorg. Chem. 1999, 38, 2676.
20.   Chmielewski, P. J.; Latos-Grazù yn´ski, L.; Schmidt, I. Inorg. Chem. 2000, 39, 5475.
21.   Chmielewski, P. J.; Latos-Grazù yn´ski, L. Inorg. Chem. 2000, 39, 5639.
22.   Rachlewicz, K.; Wang, S.-L.; Ko, J.-L.; Hung, C.-H.; Latos-Grazù yn´ski, L. J. Am. Chem. Soc. 2004, 126, 4420.
23.   Maeda, H.; Osuka, A.; Ishikawa, Y.; Aritome, I.; Hisaeda, Y.; Furuta, H. Org. Lett. 2003, 5, 1293.
24.   Bohle, D. S.; Chen, W.-C.; Hung, C.-H. Inorg. Chem. 2002, 41, 3334.
25.   Steüpien´, M.; Latos-Grazù yn´ski, L. Acc. Chem. Res. 2005, 38, 88.
26.   Hung, C.-H.; Chang, F.-C.; Lin, C.-Y.; Rachlewicz, K.; Steüpien´, M.; Latos-Grazù yn´ski, L.; Lee, G.-H.; Peng, S.-M. Inorg. Chem. 2004, 43, 4118.
27.   Steüpien´, M.; Latos-Grazù yn´ski, L.; Szterenberg, L.; Panek, J.; Latajka, Z. J. Am. Chem. Soc. 2004, 126, 4566.
28.   Steüpien´, M.; Latos-Grazù yn´ski, L. Chem.sEur. J. 2001, 7, 5113.
29.   Lash, T. D.; Colby, D. A.; Graham, S. R.; Ferrence, G. M.; Szczepura, L. F. Inorg. Chem. 2003, 42, 7326.
30.   Lash, T. D.; Rasmussen, J. M.; Bergman, K. M.; Colby, D. A. Org. Lett. 2004, 6, 549.
31.   Pawlicki, M.; Latos-Grazù yn´ski, L.; Szterenberg, L. Inorg. Chem. 2005, 44, 9779.
32.   van Koten, G.; James, S. L.; Jastrzebski, J. T. B. H. In ComprehensiVe Organometallic Chemistry II; Wardell, J. L., Abel, E. W. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science Ltd.: London, 1995; Chapter 3.
33.   Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, U.K., 1994.
34.   Chounan, Y.; Ibuka, T.; Yamamoto, Y. Chem. Commun. 1994, 2003.
35.   Fernandez de la Pradilla, R.; Rubio, M. B.; Marino, J. P.; Viso, A. Tetrahedron Lett. 1992, 33, 4985.
36.   Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900.
37.   Krause, N.; Gerold, A. Angew. Chem., Int. Ed. 1997, 36, 186.
38.   Furuta, H.; Maeda, H.; Osuka, A. J. Am. Chem. Soc. 2000, 122, 803.
39.   Maeda, H.; Osuka, A.; Furuta, H. J. Am. Chem. Soc. 2003, 125, 15690.
40.   Eujen, H.; Hoge, B.; Brauer, D. J. J. Organomet. Chem. 1996, 519, 7.
41.   Neumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482.
42.   Willert-Porada, M. A.; Burton, D. J.; Baenzinger, N. C. Chem. Commun. 1989, 1633.
43.   Navon, N.; Golub, G.; Cohen, H.; Meyerstein, D. Organometallics 1995, 14, 5670.
44.   Maeda, H.; Ishikawa, Y.; Matsuda, T.; Osuka, A.; Furuta, H. J. Am. Chem. Soc. 2003, 125, 11822.
45.   Furuta, H.; Maeda, H.; Osuka, A. Org. Lett. 2002, 4, 181.
46.   Furuta, H.; Ishizuka, T.; Osuka, A.; Uwatoko, Y.; Ishikawa, Y. Angew. Chem., Int. Ed. 2001, 40, 2323.
47.   Bru¨ckner, C.; Barta, C. A.; Brin´as, R. P.; Krause Bauer, J. A. Inorg. Chem. 2003, 42, 1673.
48.   Will, S.; Lex, J.; Vogel, E.; Schmickler, H.; Gisselbrecht, J.-P.; Haubtman, C.; Bernard, M.; Gross, M. Angew. Chem., Int. Ed. 1997, 36, 357.
49.   Bru¨ckner, C.; Brinas, R. P.; Krause-Bauer, J. A. Inorg. Chem. 2003, 42, 4495.
50.   Pacholska, E.; Espinoza, E.; Guilard, R. Dalton Trans. 2004, 3181.
51.   Brown, T. G.; Hoffman, B. M. Mol. Phys. 1980, 39, 1073.
52.   Latos-Grazù yn´ski, L.; Jezierski, A. Inorg. Chim. Acta 1985, 1985, 106.
53.   Lisowski, J.; Grzeszczuk, M.; Latos-Grazù yn´ski, L. Inorg. Chim. Acta 1989, 161, 153.
54.   Sridevi, B.; Narayanan, S. J.; Srinivasan, A.; Chandrashekar, T. K.; Subramanian, J. J. Chem. Soc., Dalton Trans. 1998, 1979.
55.   Mitrikas, G.; Calle, C.; Schweiger, A. Angew. Chem., Int. Ed. 2005, 3301.
56.   Hathaway, B. J. Struct. Bonding (Berlin) 1984, 37, 55.
57.   Orti, E.; Sanchez-Marin, J.; Merchan, M.; Tomas, F. J. Phys. Chem. 1987, 91, 545.
58.   Gallaso, V.; Klasinic, L.; Sablijc, A.; Trinajstic, N.; Pappalardo, G. C.; Steglich, W. J. J. Chem. Soc., Perkin Trans. 2 1981, 127.
59.   Scheidt, W. R.; Reed, C. R. Chem. ReV. 1981, 81, 543.
60.   Koerner, R.; Olmstead, M. M.; Ozarowski, A.; Phillips, S. L.; Van Calcar, P. M.; Winkler, K.; Balch, A. L. J. Am. Chem. Soc. 1998, 120, 1274.
61.   Phillips, S.; Noll, B. C.; Olmstead, M. M.; Balch, A. L. Can. J. Chem. 2001, 79, 922.
62.   Balch, A. L.; Mazzanti, M.; Noll, B. C.; Olmstead, M. M. J. Am. Chem. Soc. 1993, 115, 12206.
63.   Steüpien´, M.; Latos-Grazù yn´ski, L. Org. Lett. 2003, 5, 3379.
64.   Hung, C.-H.; Chen, W.-C.; Lee, G.-H.; Peng, S.-M. Chem. Commun. 2002, 1516.
65.   Hung, C.-H.; Wang, S.-L.; Ko, J.-L.; Peng, C.-H.; Hu, C.-H.; Lee, M.-T. Org. Lett. 2004, 6, 1393.
66.   Colby, D. A.; Ferrence, G. M.; Lash, T. D. Angew. Chem., Int. Ed. 2004, 43, 1346.
67.   Steüpien´, M.; Latos-Grazù yn´ski, L.; Szterenberg, L. J. Org. Chem. 2007, 72, 2259.
68.   Mys´liborski, R.; Latos-Grazù yn´ski, L. Eur. J. Org. Chem. 2005, 5039.
69.   Balch, A. L.; Latos-Grazù yn´ski, L.; Noll, B. C.; Olmstead, M. M.; Safari, N. J. Am. Chem. Soc. 1993, 115, 9056.
70.   Kalish, H.; Latos-Grazù yn´ski, L.; Balch, A. L. J. Am. Chem. Soc. 2000, 122, 12478.
71.   Kalish, H.; Lee, H. M.; Olmstead, M. M.; Latos-Grazù yn´ski, L.; Rath, S. P.; Balch, A. L. J. Am. Chem. Soc. 2003, 125, 4674.
72.   Sheldrick, G. M. SHELXL97, Program for Crystal Structure Solution; University of Go¨ttingen: Go¨ttingen, Germany, 1997.
73.   Sheldrick, G. M. SHELXL97, Program for Crystal Structure Refinement; University of Go¨ttingen: Go¨ttingen, Germany, 1997.

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