Synthesis of an oxorhenium(V) corrolate from porphyrin with detrifluoromethylation and ring contraction

Abstract

Metallation of highly electron deficient 5,10,15,20-tetrakis(trifluoromethyl)porphyrin 1 with [Re₂(CO)₁₀] in refluxing PhCN resulted in a novel synthesis of oxorhenium(V) 5,10,15-tris(trifluoromethyl)corrolate 2 characterized by single crystal X-ray crystallography.

References

1. H. Ogose, H. Kuroda and H. Murase, Jpn. Pat., Kokai Tokkyo Koho JP 02 311 478 [90 311 478](Cl. C07D487/22), 27 Dec. 1990, Appl. 89/133,037, 26 May 1989; T. P. Wijeseera and R. W. Wagner, US Pat., 5 241 062 (Cl. 540-145 C07d487/22), 31 Aug. 1993, Appl. 5,702, 19 Jan. 1993; S. G. Dimagno, M. J. Therien and R. A. Williams, J. Org. Chem., 1994, 59, 6943.
2. S. G. Dimagno, A. K. Wertsching and C. R. Ross, J. Am. Chem. Soc., 1995, 117, 8279; J. G. Goll, K. T. Moore, A. Ghosh and M. J. Therien, J. Am. Chem. Soc., 1996, 118, 8344.
3. In Metalloporphyrins in Catalytic Oxidations, ed. R. A. Sheldon, Marcel Dekker, New York, 1994; B. Meunier, Chem. Rev., 1992, 92, 1411; P. E. Ellis Jr. and J. E. Lyons, Coord. Chem. Rev., 1990, 105, 181; T. P. Wijesekera, J. E. Lyons and P. E. Ellis Jr, Catal. Lett., 1996, 36, 69.
4. M. Tsutsui, C. P. Hrung, D. Ostfeld, T. S. Srivastava, D. L. Cullen and E. F. Meyer Jr., J. Am. Chem. Soc., 1975, 97, 1975; A.-M. Lebuis and A. L. Beauchamp, Can. J. Chem., 1993, 71, 2060; C. Bolzati, F. Tisato, F. Refosco, G. Bandoli and A. Dolmella, Inorg. Chem., 1996, 35, 6221; B. Noll, S. Noll, P. Leibnitz, H. Spies, P. E. Schulze, W. Semmler and B. Johannsen, Inorg. Chim. Acta, 1997, 255, 399; S. Bélanger, S. Fortin and A. L. Beauchamp, Can. J. Chem., 1997, 75, 37; B. Dirghangi, K. Menon, M. A. Pramanik and A. Chakravorty, Inorg. Chem., 1997, 36, 1095.
5. For the diphosphine rhenium porphyrin, average Re-N bond length was 2.059(5)Å; J. P. Collman, J. M. Garner, K. Kim and J. A. Ibers, Inorg. Chem., 1988, 27, 4513 for the nitridorhenium(v) porphyrins, Re-N bond lengths range from 2.074(4) to 2.086(4)Å; J. W. Buchler, A. D. Cian, J. Fischer, S. B. Kruppa and R. Weiss, Chem. Ber., 1990, 123, 2247.
6. J. Jubb, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1992, 114, 6571; U. Piarulli, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Chem. Soc., Chem. Commun., 1994, 895.
7. R. Paolesse, S. Licoccia, G. Bandoli, A. Dolmella and T. Boschi, Inorg. Chem., 1994, 33, 1171; S. Licoccia, E. Tassoni, R. Paolesse and T. Boschi, Inorg. Chim. Acta, 1995, 235, 15.