Synthesis and characterization of an oxasapphyrin-uranyl complex

Abstract

Reaction of monooxasapphyrin with uranyl diacetate in the presence of triethylamine leads to the formation of a stable, in-plane aromatic uranyl complex.

References

1. R. B. Woodward, in Aromaticity: An Internatinal Symposium Sheffield, 1966, Special Publication no. 21, The Chemical Society, London, 1966.
2. (a) V. J. Bauer, D. L. J. Clive, D. Dolphin, J. B. Paine III, F. L. Harris, M. M. King, J. Loder, S.-W. C. Wang and R. B. Woodward, J. Am. Chem. Soc., 1983, 105, 6429; (b) M. J. Broadhurst, R. Grigg and A. W. Johnson, J. Chem. Soc., Perkin Trans. 1, 1972, 2111; (c) M. J. Broadhurst, R. Grigg and A. W. Johnson, Chem. Commun., 1969, 23; (d) J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810; (e) A. K. Burrell, J. L. Sessler, M. Cyr, E. McGhee and J. A. Ibers, Angew. Chem., 1991, 103, 83; Angew. Chem., Int. Ed. Engl., 1991, 30, 91; (f) J. L. Sessler, J. Lisowski, K. A. Boudreaux, V. Lynch, J. Barry and T. J. Kodadek, J. Org. Chem., 1995, 60, 5975; (g) L. Latos-Grazynski and K. Rachlewics, Chem. Eur. J., 1995, 1, 68; (h) R. Paolesse, S. Licoccia, M. Spagnoli, T. Boschi, R. G. Khoury and K. M. Smith, J. Org. Chem., 1997, 62, 5133; (i) C. Brückner, E. D. Sternberg, R. W. Boyle and D. Dolphin, Chem. Commun., 1997, 1689.
3. J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford, 1997, pp. 453–489 and references therein.
4. A. K. Burrell, M. C. Cyr, V. Lynch and J. L. Sessler, J. Chem. Soc., Chem. Commun., 1991, 1710.
5. V. W. Day, T. J. Marks and W. A. Wachter, J. Am. Chem. Soc., 1975, 97, 4519; T. J. Marks and D. R. Stojakovic, J. Am. Chem. Soc., 1978, 1695; E. A. Cuellar, D. R. Stojakovic and T. J. Marks, Inorg. Synth., 1980, 20, 97.
6. (a) A. Gossauer, Bull. Soc. Chim. Belg., 1983, 92, 793; (b) A. K. Burrell, G. Hemmi, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 4690.
7. J. L. Sessler, M. J. Cyr and A. K. Burrell, Synlett, 1991, 127.
8. J. L. Sessler, M. C. Hoehner, A. Gebauer, A. Andreivsky and V. Lynch, J. Org. Chem., 1997, 62, 9251.
9. For typical proton NMR chemical shift data for sapphyrin see: J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford, 1997, pp. 253–302 and references therein.
10. J. L. Sessler, M. Cyr and A. K. Burrell, Tetrahedron, 1992, 48, 9661.
11. J. R. Brand and J. W. Cobble, Inorg. Chem., 1970, 9, 912.