Pyriporphyrinone: A new 18-π aromatic porphyrinoid

Synthesis

Volumn , Issue 3, 1997, Pages 273-275

  Schönemeier, Thomas ^a   Breitmaier, Eberhard ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

cyclocondensation; porphyrins; tautomers

Indexed keywords

PORPHYRIN DERIVATIVE; PYRIPORPHYRINONE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROPHOTOMETRY; STEREOCHEMISTRY;

EID: 0030945593     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1178     Document Type: Article

References (34)

1. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
2. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
3. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
4. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
5. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
6. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
7. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
8. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
9. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
10. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
11. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
12. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
13. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
14. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
15. Sessler, J.L.; Weghorn, S.J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177, and references cited therein. Wessel, T.; Franck, B.; Möllter, M.; Rodewald, U.; Läge, M. Angew. Chem. 1993, 105, 1201; Angew. Chem. Int. Ed. Engl. 1993, 32, 1148. Sessler, J.L.; Weghorn, S.J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306. Sessler, J.L.; Mody, T.D.; Ford, D.A.; Lynch, V. Angew. Chem. 1992, 104, 461; Angew. Chem. Int. Ed. Engl. 1992, 31, 452. Pohl, M.; Schmickler, H.; Lex, J.; Vogel, E. ibid. 1991, 103, 1737; 1991, 30, 1693. König, H.; Eickmeier, C.; Möller, M.; Rodewald, U.; Franck, B. ibid. 1990, 102, 1437; 1990, 29, 1393. Beckmann, S., Wessel, T.; Franck, B.; Hönle, W.; Borrmann, H.; von Schnering, H.G. ibid. 1990, 102, 1439; 1990, 29, 1395. Bröring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Nendel, M.; Chen, J.; Plattner, D.A.; Houk, K.N.; Vogel, E. Angew. Chem. 1995, 107, 2709; Angew. Chem. Int. Ed. Engl. 1995, 21, 34.
16. Dolphin, D.; Felton, R.H.; Borg, D.C.; Fajer, J. J. Am. Chem. Soc. 1970, 92, 743. Barkigia, K.M.; Renner, M.W.; Xie, H.; Smith, K.M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 7894, and references cited therein. M.J. Broadhurst, M.J.; Grigg, R.; Johnson, A.W. J. Chem. Soc. 1971, 3681. Gosmann, M.; Frank, B. Angew. Chem. 1986, 98, 1107; Angew. Chem. Int. Ed. Engl. 1986, 25, 1100. Vogel, E. Pure Appl. Chem. 1993, 65, 143, and references cited therein.
17. Dolphin, D.; Felton, R.H.; Borg, D.C.; Fajer, J. J. Am. Chem. Soc. 1970, 92, 743. Barkigia, K.M.; Renner, M.W.; Xie, H.; Smith, K.M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 7894, and references cited therein. M.J. Broadhurst, M.J.; Grigg, R.; Johnson, A.W. J. Chem. Soc. 1971, 3681. Gosmann, M.; Frank, B. Angew. Chem. 1986, 98, 1107; Angew. Chem. Int. Ed. Engl. 1986, 25, 1100. Vogel, E. Pure Appl. Chem. 1993, 65, 143, and references cited therein.
18. Dolphin, D.; Felton, R.H.; Borg, D.C.; Fajer, J. J. Am. Chem. Soc. 1970, 92, 743. Barkigia, K.M.; Renner, M.W.; Xie, H.; Smith, K.M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 7894, and references cited therein. M.J. Broadhurst, M.J.; Grigg, R.; Johnson, A.W. J. Chem. Soc. 1971, 3681. Gosmann, M.; Frank, B. Angew. Chem. 1986, 98, 1107; Angew. Chem. Int. Ed. Engl. 1986, 25, 1100. Vogel, E. Pure Appl. Chem. 1993, 65, 143, and references cited therein.
19. Dolphin, D.; Felton, R.H.; Borg, D.C.; Fajer, J. J. Am. Chem. Soc. 1970, 92, 743. Barkigia, K.M.; Renner, M.W.; Xie, H.; Smith, K.M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 7894, and references cited therein. M.J. Broadhurst, M.J.; Grigg, R.; Johnson, A.W. J. Chem. Soc. 1971, 3681. Gosmann, M.; Frank, B. Angew. Chem. 1986, 98, 1107; Angew. Chem. Int. Ed. Engl. 1986, 25, 1100. Vogel, E. Pure Appl. Chem. 1993, 65, 143, and references cited therein.
20. Dolphin, D.; Felton, R.H.; Borg, D.C.; Fajer, J. J. Am. Chem. Soc. 1970, 92, 743. Barkigia, K.M.; Renner, M.W.; Xie, H.; Smith, K.M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 7894, and references cited therein. M.J. Broadhurst, M.J.; Grigg, R.; Johnson, A.W. J. Chem. Soc. 1971, 3681. Gosmann, M.; Frank, B. Angew. Chem. 1986, 98, 1107; Angew. Chem. Int. Ed. Engl. 1986, 25, 1100. Vogel, E. Pure Appl. Chem. 1993, 65, 143, and references cited therein.
21. Dolphin, D.; Felton, R.H.; Borg, D.C.; Fajer, J. J. Am. Chem. Soc. 1970, 92, 743. Barkigia, K.M.; Renner, M.W.; Xie, H.; Smith, K.M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 7894, and references cited therein. M.J. Broadhurst, M.J.; Grigg, R.; Johnson, A.W. J. Chem. Soc. 1971, 3681. Gosmann, M.; Frank, B. Angew. Chem. 1986, 98, 1107; Angew. Chem. Int. Ed. Engl. 1986, 25, 1100. Vogel, E. Pure Appl. Chem. 1993, 65, 143, and references cited therein.
22. Furuta, H.; Asano, T.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 767.
23. To simplify matters the trivial name tripyrrane is used here instead of 2,5-bis[(pyrrol-2-yl)methyl]pyrrole.
24. Berlin, K.; Steinbeck, C.; Breitmaier, E. Synthesis 1996, 336.
25. Berlin, K.; Breitmaier, E. Angew. Chem. 1994, 106, 229; Angew. Chem. Int. Ed. Engl. 1994, 33, 219.
26. Berlin, K.; Breitmaier, E. Angew. Chem. 1994, 106, 229; Angew. Chem. Int. Ed. Engl. 1994, 33, 219.
27. Berlin, K.; Breitmaier, E. Angew. Chem. 1994, 106, 1356; Angew. Chem. Int. Ed. Engl. 1994, 33, 1246.
28. Berlin, K.; Breitmaier, E. Angew. Chem. 1994, 106, 1356; Angew. Chem. Int. Ed. Engl. 1994, 33, 1246.
29. Lash, T.D. Angew. Chem. 1995, 107, 2703; Angew. Chem. Int. Ed. Engl. 1995, 34, 2533.
30. Lash, T.D. Angew. Chem. 1995, 107, 2703; Angew. Chem. Int. Ed. Engl. 1995, 34, 2533.
31. Baldo, M.A.; Chessa, G.; Marangoni, G.; Pitteri, B. Synthesis 1987, 720.
32. Result of searching in BEILSTEIN online [COPYRIGHT (C) 1995 Beilstein Informationssysteme GmbH] on 10 July 1996 and searching in REGISTRY online [COPYRIGHT (C) 1995 American Chemical Society (ACS)] on 04 December 1995.
33. Doering, W. von E.; Knox, L.H. J. Org. Chem. 1957, 79, 352.
34. During the evaluation of this paper by the referees, the synthesis of the pyriporphyrinones 3 was published independently: Lash, T.D.; Chancy, S.T. Chem. Eur. J. 1996, 2, 944. We thank one of the referees for pointing out this work.