Synthesis and characterization of intramolecular N-strapped porphyrins

Abstract

The first successful synthesis and characterization of intramolecular N-strapped porphyrins and the separation of a set of enantiomers are described.

References

1. For reviews, see J. L. Sessler, Angew. Chem., Int. Ed. Engl., 1994, 33, 1348; B. Franck and A. Nonn, ibid., 1995, 34, 1795; E. Vogel, Pure Appl. Chem., 1996, 68, 1355.
2. E. Vogel, M. Kocher, H. Schmickler and J. Lex, Angew. Chem., Int. Ed. Engl., 1986, 25, 257; J. L. Sessler and A. K. Burrell, Top. Curr. Chem., 1991, 161, 177; H. Furuta, T. Asano and T. Ogawa, J. Am. Chem. Soc., 1994, 116, 767; P. J. Chmielewski, L. Latos-Grazynski, K. Rachlewicz and T. Glowiak, Angew. Chem., Int. Ed. Engl., 1994, 33, 779; J. L. Sessler, ibid., 1994, 33, 1348; T. D. Lash, ibid., 1995, 34, 2553; J. L. Sessler, S. W. Weghorn, Y. Hishaeda and V. Lynch, Chem. Eur. J., 1995, 1, 56; B. Franck and A. Nonn, Angew. Chem., Int. Ed. Engl., 1995, 34, 1795; T.. D. Lash and S. T. Chaney, Chem. Eur. J., 1996, 2, 944; T. D. Lash and M. J. Hayes, Angew. Chem., Int. Ed. Engl., 1997, 36, 840; K. K. Dailey, G. P. A. Yap, A. L. Rheingold and T. B. Rauchfuss, ibid., 1996, 35, 1833.
3. D. K. Lavallee, The Chemistry and Biochemistry of N-Substituted Porphyrins, VCH, Weinheim, 1987 and references cited therein; H. J. Callot, R. Cromer, A. Louati, B. Mets and B. J. Chevrier, J. Am. Chem. Soc., 1987, 109, 2946; A. L. Balch, C. R. Cornman, L. Latos-Grazynski and M. M. Olstead, ibid., 1990, 112, 7552; K. Konishi, Y. Takahata, T. Aida and S. Inoue, ibid., 1993, 115, 1169; J.-i. Setsune and H. Takeda, Tetrahedron Lett., 1995, 36, 5903.
4. R. G. Little, J. A. Anton, P. A. Loach and J. A. Ibers, J. Heterocycl. Chem., 1975, 12, 343.
5. D. Kuila, D. K. Lavallee, C. K. Schauer and O. P. Anderson, J. Am. Chem. Soc., 1984, 106, 448.
6. H. Scheer and J. J. Katz, in Porphyrin and Metalloporphyrins, ed. K. M. Smith, Elsevier, Amsterdam, 1975, p. 487; D. K. Lavallee, I. Morgenstern-Badarau, M. Lange and P. Gans, Inorg. Chem., 1979, 18, 1776.