Enantiomerically Pure "Winged" Spirane Porphyrazinoctaols

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 7, 1997, Pages 760-761

  Cook, Andrew S ^a   Williams, D Bradley G ^a   White, Andrew J P ^a   Williams, David J ^a   Lange, Steven J ^b   Barrett, Anthony G M ^a   Huffman, Brian M ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Chirality; Cyclic voltammetry; Porphyrinoids; Protecting groups; Spiro compounds

Indexed keywords

EID: 0030754169     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199707601     Document Type: Article

References (21)

1. S.V. Ley, M. Woods, A. Zanotti-Gerosa, Synthesis 1992, 52; S. V. Ley, R. Leslie, P. D. Tiffin, M. Woods, Tetrahedron Lett, 1992, 33, 4767; R. Downham, K. S. Kim, S. V. Ley, M. Woods, ibid. 1994, 35, 769; D. A. Entwistle, A. B. Hughes, S. V. Ley, G. Visentin, ibid. 1994, 35, 111.
2. S.V. Ley, M. Woods, A. Zanotti-Gerosa, Synthesis 1992, 52; S. V. Ley, R. Leslie, P. D. Tiffin, M. Woods, Tetrahedron Lett, 1992, 33, 4767; R. Downham, K. S. Kim, S. V. Ley, M. Woods, ibid. 1994, 35, 769; D. A. Entwistle, A. B. Hughes, S. V. Ley, G. Visentin, ibid. 1994, 35, 111.
3. S.V. Ley, M. Woods, A. Zanotti-Gerosa, Synthesis 1992, 52; S. V. Ley, R. Leslie, P. D. Tiffin, M. Woods, Tetrahedron Lett, 1992, 33, 4767; R. Downham, K. S. Kim, S. V. Ley, M. Woods, ibid. 1994, 35, 769; D. A. Entwistle, A. B. Hughes, S. V. Ley, G. Visentin, ibid. 1994, 35, 111.
4. S.V. Ley, M. Woods, A. Zanotti-Gerosa, Synthesis 1992, 52; S. V. Ley, R. Leslie, P. D. Tiffin, M. Woods, Tetrahedron Lett, 1992, 33, 4767; R. Downham, K. S. Kim, S. V. Ley, M. Woods, ibid. 1994, 35, 769; D. A. Entwistle, A. B. Hughes, S. V. Ley, G. Visentin, ibid. 1994, 35, 111.
5. C. J. Schramm, B. M. Hoffman, Inorg. Chem. 1980, 19, 383.
6. C. S. Velázquez, W. E. Broderick, M. Sabat, A. G. M. Barrett, B. M. Hoffman, J. Am. Chem. Soc. 1990, 112, 7408; C. S. Velázquez, G. A. Fox, W. E. Broderick, K. A. Andersen, O. P. Anderson, A. G. M. Barren, B. M. Hoffman, ibid. 1992, 114, 7416; C. S. Velázquez, T. F. Baumann, M. M. Olmstead, H. Hope, A. G. M. Barrett, B. M. Hoffman, ibid. 1993, 115, 9997.
7. C. S. Velázquez, W. E. Broderick, M. Sabat, A. G. M. Barrett, B. M. Hoffman, J. Am. Chem. Soc. 1990, 112, 7408; C. S. Velázquez, G. A. Fox, W. E. Broderick, K. A. Andersen, O. P. Anderson, A. G. M. Barren, B. M. Hoffman, ibid. 1992, 114, 7416; C. S. Velázquez, T. F. Baumann, M. M. Olmstead, H. Hope, A. G. M. Barrett, B. M. Hoffman, ibid. 1993, 115, 9997.
8. C. S. Velázquez, W. E. Broderick, M. Sabat, A. G. M. Barrett, B. M. Hoffman, J. Am. Chem. Soc. 1990, 112, 7408; C. S. Velázquez, G. A. Fox, W. E. Broderick, K. A. Andersen, O. P. Anderson, A. G. M. Barren, B. M. Hoffman, ibid. 1992, 114, 7416; C. S. Velázquez, T. F. Baumann, M. M. Olmstead, H. Hope, A. G. M. Barrett, B. M. Hoffman, ibid. 1993, 115, 9997.
9. N. S. Mani, L. S. Beall, T. Miller, O. P. Anderson, H. Hope, S. R. Parkin, D. J. Williams, A. G. M. Barrett, B. M. Hoffman, J. Chem. Soc. Chem. Commun. 1994, 2095; D. M. Eichhorn, S. Yang, W. Jarrell, T. F. Baumunn, L. S. Beall, A. J. P. White, D. J. Williams, A. G. M. Barrett, B. M. Hoffman, ibid. 1995, 1703.
10. N. S. Mani, L. S. Beall, T. Miller, O. P. Anderson, H. Hope, S. R. Parkin, D. J. Williams, A. G. M. Barrett, B. M. Hoffman, J. Chem. Soc. Chem. Commun. 1994, 2095; D. M. Eichhorn, S. Yang, W. Jarrell, T. F. Baumunn, L. S. Beall, A. J. P. White, D. J. Williams, A. G. M. Barrett, B. M. Hoffman, ibid. 1995, 1703.
11. Kopranenkov et al. have reported a synthesis of 2,3-di(alkoxy)- and 2,7,12,17tetra(alkoxy)porphyrazines. However, in our hands, this procedure failed to provide characterizable pigments: V. N. Kopranenkov, L. S. Goncharova, E. A. Luk'yanets, J. Org. Chem. USSR 1979, 15, 962; V. N. Kopranenkov, L. S. Goncharova, L. E. Marinina, E. A. Luk'yanets, Chemistry of Heterocyclic Compounds USSR 1982, 18, 1269. The synthesis of some crown ether annulated porphyrins has been reported: H. Uno, T. Ogawa, N. Ono, Tetrahedron Lett. 1996, 37, 3133.
12. Kopranenkov et al. have reported a synthesis of 2,3-di(alkoxy)- and 2,7,12,17tetra(alkoxy)porphyrazines. However, in our hands, this procedure failed to provide characterizable pigments: V. N. Kopranenkov, L. S. Goncharova, E. A. Luk'yanets, J. Org. Chem. USSR 1979, 15, 962; V. N. Kopranenkov, L. S. Goncharova, L. E. Marinina, E. A. Luk'yanets, Chemistry of Heterocyclic Compounds USSR 1982, 18, 1269. The synthesis of some crown ether annulated porphyrins has been reported: H. Uno, T. Ogawa, N. Ono, Tetrahedron Lett. 1996, 37, 3133.
13. Kopranenkov et al. have reported a synthesis of 2,3-di(alkoxy)- and 2,7,12,17tetra(alkoxy)porphyrazines. However, in our hands, this procedure failed to provide characterizable pigments: V. N. Kopranenkov, L. S. Goncharova, E. A. Luk'yanets, J. Org. Chem. USSR 1979, 15, 962; V. N. Kopranenkov, L. S. Goncharova, L. E. Marinina, E. A. Luk'yanets, Chemistry of Heterocyclic Compounds USSR 1982, 18, 1269. The synthesis of some crown ether annulated porphyrins has been reported: H. Uno, T. Ogawa, N. Ono, Tetrahedron Lett. 1996, 37, 3133.
14. S. Ghosal, G. P. Luke, K. S. Kyler, J. Org. Chem. 1987, 52, 4296.
15. P. Deslongchamps, Stereoelectronic Effects in Organic Synthesis, Pergamon, Oxford, 1983.
16. 0|), 2θ≤ 110°] and 602 parameters. The absolute chiraJity of the structure could not be determined crystallographically and was assigned on the basis of the known absolute stereochemistry of 1 and the expected stereochemical bias of dispoke protections [1,7]. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100184. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: Int. code +(1223)336-03.1; e-mail: deposit@chemcrys.cam.ac.uk).
17. +); found: 1107.4706.
18. M. Goutermann in The Porphyrins, Vol. 2 (Ed.: D. Dolphin), Academic Press, New York, 1978, chap. 1.
19. -1.
20. For electroreduction of octakis(methylthio)porphyrazines in pyridine, see L. A. Bottomley, W. J. H. Chiou, J. Electroanal. Chem. 1986, 198, 331.
21. This macrocycle was synthesized by a slight modification of the procedure of Fitzgerald and co-workers: J. Fitzgerald. W. Taylor, H. Owen, Synthesis 1991, 686.