Unexpected isolation and characterization of a chloroiron complex with a 10-acetylcorrole ligand

Journal of Porphyrins and Phthalocyanines

Volumn 12, Issue 10, 2008, Pages 1111-1117

  Bröring, Martin ^a   Köhler, Silke ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

2,2' bidipyrrin; Corrole; Iron; Macrocyclization; Porphyrinoids; X ray structure

Indexed keywords

EID: 58249116661     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S1088424608000479     Document Type: Article

References (59)

1. Smith KM. In The Porphyrin Handbook, Vol. 1, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: San Diego, CA, 2000; pp 119-148.
2. For examples, see: a) Eschenmoser A. Pure Appl. Chem. 1969; 20: 1-23.
3. b) Engel J and Inhoffen HH. Liebigs Ann. Chem. 1977; 767-771.
4. c) Xie H and Smith KM. Tetrahedron Lett. 1992; 33: 1197-1200.
5. d) Barkigia KM, Renner MW, Xie H, Smith KM and Fajer J. J. Am. Chem. Soc. 1993; 115: 7894-7895.
6. e) Vogel E, Binsack B, Hellwig Y, Erben C, Heger A, Lex J and Wu Y-D. Angew. Chem., Int. Ed. Engl. 1997; 36: 2612-2616.
7. f) Vogel E, Bröring M, Erben C, Demuth R, Lex J, Nendel M and Houk KN. Angew. Chem., Int. Ed. Engl. 1997; 36: 353-357.
8. g) Paolesse R. In The Porphyrin Handbook, Vol. 2, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: San Diego, CA, 2000; pp 201-232.
9. h) Bröring M, Cónsul Tejero E, Pfister A, Brandt CD and Pérez Torrente JJ. Chem. Commun. 2002; 3058-3059.
10. i) Bröring M, Brandt CD and Cónsul Tejero E. Z. Anorg. Allg. Chem. 2005; 631: 1793-1798.
11. j) Bröring M and Cónsul Tejero E. J. Organomet. Chem. 2005; 690: 5290-5299.
12. k) Bröring M, Cordes M and Köhler S. Z. Anorg. Allg. Chem. 2008; 634: 125-130.
13. l) Dogutan DK, Ptaszek M and Lindsey JS. J. Org. Chem. 2007; 72: 5008-5011.
14. m) Sharada DS, Muresan AZ, Muthukumaran K and Lindsey JS. J. Org. Chem. 2005; 70: 3500- 3510.
15. a) Bröring M. Synthesis 2000; 1291-1294.
16. b) Bröring M, Brandt CD, Lex J, Humpf H-U, Bley-Escrich J and Gisselbrecht J-P. Eur. J. Inorg. Chem. 2001; 2549-2556.
17. c) Bröring M, Brandt CD, Bley-Escrich J and Gisselbrecht J-P. Eur. J. Inorg. Chem. 2002; 910-917.
18. d) Bröring M, Link S, Brandt CD and Cónsul Tejero E. Eur. J. Inorg. Chem. 2007; 1661-1670.
19. e) Bröring M, Krüger R, Link S, Kleeberg C, Köhler S, Xie X, Ventura B and Flamigni L. Chem. Eur. J. 2008; 14: 2976-2983.
20. Bröring M and Hell C. Chem. Commun. 2001, 2336-2337.
21. b) Bröring M, Hell C and Brandt CD. Chem. Commun. 2007; 1861-1862.
22. c) Bröring M, Hell C, Steiner M and Brandt CD. Z. Anorg. Allg. Chem. 2007; 633: 1082-1086.
23. Bröring M, Brégier F, Cónsul Tejero E, Hell C and Holthausen MC. Angew. Chem. Int. Ed. 2007; 46: 445-448.
24. a) Jérôme F, Barbe J-M, Gros CP, Guilard R, Fischer J and Weiss R. New J. Chem. 2001; 25: 93-101.
25. b) Bröring M, Hell C, Brandt CD and Cónsul Tejero E. J. Porphyrins Phthalocyanines 2003; 7: 214-219.
26. Neya S, Nishinaga K, Ohyama K and Funasaki N. Tetrahedron Lett. 1998; 39: 5217-5220.
27. b) Falk H and Chen Q-Q. Monatsh. Chem. 1996; 127: 69-75.
28. c) Aukauloo MA and Guilard R. New J. Chem. 1994; 18: 1205-1207.
29. d) Sessler JL, Brucker EA, Weghom SL, Kisters M, Schäfer M, Lex J and Vogel E. Angew. Chem., Int. Ed. Engl. 1994; 33: 2308-2312.
30. e) Sessler JL, Gebauer A and Vogel E. In The Porphyrin Handbook, Vol. 2, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: San Diego, CA,2000;pp 1-54.
31. Bröring M, Hell C, Brégier F, Burghaus O and Cónsul Tejero E. Inorg. Chem. 2007; 46: 5477-5479.
32. For similar ring-expanded products, the so-called homoporphyrins, please refer to a) Liddell PA, Olmstead MM and Smith KM. J. Am. Chem. Soc. 1990; 112: 2038-2040.
33. b) Liddell PA, Gerzevske KR, Lin JJ, Olmstead MM and Smith KM. J. Org. Chem. 1993; 58: 6681-6691.
34. Bröring M, Köhler S and Kleeberg C. Angew. Chem. Int. Ed. 2008; 47: 5658-5661.
35. For even smaller tripyrrolic examples, the subporphyrins and subphthalocyanines, see: Inokuma Y and Osuka A. Dalton Trans. 2008; 2517-2526.
36. Claessens CG, Ganzalez-Rodriguez D and Torres T. Chem. Rev. 2002; 102: 835-853.
37. Bröring M, Köhler S, Link S, Burghaus O, Pietzonka C, Kelm H and Krüger H-J. Chem. Eur. J. 2008; 14: 4006-4016.
38. b) Bröring M and Köhler S. Z. Anorg. Allg. Chem. 2008; 634: 1469-1471.
39. Bröring M, Griebel D, Hell C and Pfister A. J. Porphyrins Phthalocyanines 2001; 5: 708-714.
40. Sessler JL, Mozafari A and Johnson MR. Org. Synth. 1991; 70: 68-78.
41. Sheldrick GM. SHELXS-97 Program for Structure Determination, University of Göttingen, Göttingen, Germany, 1997.
42. Sheldrick GM. SHELXL-97 Program for Structure Refinement, University of Göttingen, Göttingen, Germany, 1997.
43. Vogel E, Will S, Schulze-Tilling A, Neumann L, Lex J, Bill E, Trautwein AX and Wieghardt K. Angew. Chem. Int. Ed. Engl. 1994; 33: 731-735.
44. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M and van de Streek J. J. Appl. Cryst. 2006; 39: 453-457.
45. Zakharieva O, Schünemann V, Gerdan M, Licoccia S, Cai S, Walker FA and Trautwein AX. J. Am. Chem. Soc. 2002; 124: 6636-6648.
46. a) Vicente MGH. In The Porphyrin Handbook, Vol. 1, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: San Diego, CA, 2000; pp 149-199.
47. b) Jaquinod L. In The Porphyrin Handbook, Vol. 1, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: San Diego, CA, 2000; pp 201-237.
48. Stefanelli M, Mastroianni M, Nardis S, Liccocia S, Fronczek FR, Smith KM, Zhu W, Ou Z, Kadish KM and Paolesse R. Inorg. Chem. 2007; 46: 10791-10799.
49. b) Nardis S, Monti D and Paolesse R. Mini-Rev. Org. Chem. 2005; 2: 355- 372.
50. c) Saltsman I, Mahammed A, Goldberg I, Tkachenko E, Botoshansky M and Gross Z. J. Am. Chem. Soc. 2002; 124:7411-7420.
51. d) Nardis S, Mandoj F, Paolesse R, Fronczek FR, Smith KM, Prodi L, Montalti M and Battistini G. Eur. J. Inorg. Chem. 2007; 2345-2352.
52. e) Paolesse R, Nardis S, Venanzi M, Mastroianni M, Fronzcek FR and Vicente MGH. Chem. Eur. J. 2003; 9: 1192-1197.
53. f) Paolesse R, Nardis S, Sagone F and Khoury R. J. Org. Chem. 2001; 66:550-556.
54. g) Wasbotten IH, Wondimagegn T and Ghosh A. J. Am. Chem. Soc. 2002; 124: 8104-8116.
55. h) Saltsman I, Goldberg I and Gross Z. Tetrahedron Lett. 2003; 44: 5669-5673.
56. h) Hiroto S, Hisaka I, Shinokubo H and Osuka A. Angew. Chem. Int. Ed. 2005; 44: 6763-6766.
57. Gryko DT, Tasior M, Peterle T and Bröring M. J. Porphyrins Phthalocyanines 2006; 10: 1360-1370.
58. b) Maes W, Ngo TH, Vanderhaeghen J and Dehaen W. Org. Lett. 2007; 9: 3165-3168.
59. c) Bröring M, Milsmann C, Ruck S and Köhler S. J. Organomet. Chem. 2008; DOI:10.1016/j. jorganchem.2008.04.039.