Improved routes for the synthesis of face-to-face bismacrocycles in porphyrin and corrole series

Journal of Porphyrins and Phthalocyanines

Volumn 8, Issue 1-3, 2004, Pages 301-312

  Barbe, Jean Michel ^a   Stern, Christine ^a   Pacholska, Ewa ^a,b   Espinosa, Enrique ^a   Guilard, Roger ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b Wydzial Chem Uniwers Wroclawskiego   (Poland)

Author keywords

Bismacrocycle; Corrole; Porphyrin; Synthesis

Indexed keywords

BISCORROLE; BISPORPHYRIN; COORDINATION COMPOUND; CORROLE; MACROCYCLIC COMPOUND; PORPHYRIN; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

COMPLEX FORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLIZATION; OXIDATION REDUCTION REACTION; POLYMERIZATION; REACTION ANALYSIS; SHORT SURVEY; SYNTHESIS; X RAY DIFFRACTION;

EID: 3342979754     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/s1088424604000283     Document Type: Short Survey

References (75)

1. Smith KM. In The Porphyrin Handbook, Vol. 1, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 1-43.
2. Lindsey JS. In The Porphyrin Handbook, Vol. 1, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 45-118.
3. Smith KM. In The Porphyrin Handbook, Vol. 1, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 119-148.
4. Paolesse R. In The Porphyrin Handbook, Vol. 2, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 201-232.
5. Erben C, Will S and Kadish KM. In The Porphyrin Handbook, Vol. 2, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 233-300.
6. Guilard R, Barbe JM, Stern C and Kadish KM. In The Porphyrin Handbook, Vol. 18, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2003; pp 303-349.
7. Barbe JM and Guilard R. In The Porphyrin Handbook, Vol. 3, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 211-244.
8. Collman JP, Wagenknecht PS and Hutchison JE. Angew. Chem., Int. Ed. 1994; 33: 1537-1554.
9. Collman JP, Boulatov R and Sunderland CJ. In The Porphyrin Handbook, Vol. 11, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2003; pp 1-49.
10. Collman JP, Boulatov R, Sunderland CJ and Fu L. Chem. Rev. (Washington, DC, U. S.) 2004; 104: 561-588.
11. Kim E, Chufan EE, Kamaraj K and Karlin KD. Chem. Rev. (Washington, DC, U. S.) 2004; 104: 1077-1133.
12. Meier H, Kobuke Y and Kugimiya S-i. J. Chem. Soc., Chem. Commun. 1989: 923-924.
13. Collman JP, Tyvoll DA, Chng LL and Fish HT. J. Org. Chem. 1995; 60: 1926-1931.
14. Brettar J, Gisselbrecht J-P, Gross M and Solladié N. Chem. Commun. (Cambridge, U. K.) 2001: 733-734.
15. Tomohiro Y, Satake A and Kobuke Y. J. Org. Chem. 2001; 66: 8442-8446.
16. Fletcher JT and Therien MJ. J. Am. Chem. Soc. 2002; 124: 4298-4311.
17. Chng LL, Chang CJ and Nocera DG. J. Org. Chem. 2003; 68: 4075-4078.
18. Yagi S, Yonekura I, Awakura M, Ezoe M and Takagishi T. Chem. Commun. (Cambridge, U. K.) 2001: 557-558.
19. Jokic D, Asfari Z and Weiss J. Org. Lett. 2002; 4: 2129-2132.
20. Dudic M, Lhotak P, Stibor I, Lang K and Proskova P. Org. Lett. 2003; 5: 149-152.
21. Dudic M, Lhotak P, Stibor I, Petrickova H and Lang K. New J. Chem. 2004; 28: 85-90.
22. Mamardashvili N, Pognon G and Weiss J. J. Org. Chem. 2004: in press.
23. Gross Z, Galili N and Saltsman I. Angew. Chem., Int. Ed. 1999; 38: 1427-1429.
24. Simkhovich L, Galili N, Saltsman I, Goldberg I and Gross Z. Inorg. Chem. 2000; 39: 2704-2705.
25. Paolesse R, Nardis S, Sagone F and Khoury RG. J. Org. Chem. 2001; 66: 550-556.
26. Gryko DT. Chem. Commun. (Cambridge, U. K.) 2000: 2243-2244.
27. Gryko DT and Jadach K. J. Org. Chem. 2001; 66: 4267-4275.
28. Asokan CV, Smeets S and Dehaen W. Tetrahedron Lett. 2001; 42: 4483-4485.
29. Gryko DT and Piechota KE. J. Porphyrins Phthalocyanines 2002; 6: 81-97.
30. Gryko DT and Koszarna B. Org. Biomol. Chem. 2003; 1: 350-357.
31. Guilard R, Gryko DT, Canard G, Barbe J-M, Koszarna B, Brandès S and Tasior M. Org. Lett. 2002; 4: 4491-4494.
32. Burdet F, Espinosa E, Barbe J-M and Guilard R. submitted for publication.
33. Guilard R, Pacholwska E and Espinosa E. submitted for publication.
34. Pacholwska E, Espinosa E and Guilard R. submitted for publication.
35. Barbe JM, Burdet F, Espinosa E, Gros CP and Guilard R. J. Porphyrins Phthalocyanines 2003; 7: 365-374.
36. Gust D, Moore TA and Moore AL. Acc. Chem. Res. 2001; 34: 40-48.
37. Jordan P, Fromme P, Witt HT, Klukas O, Saenger W and Krauss N. Nature (London, U. K.) 2001; 411: 909-917.
38. Harvey PD. In The Porphyrin Handbook, Vol. 18, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2003; pp 63-250.
39. Aratani N, Osuka A, Cho HS and Kim D. J. Photochem. Photobiol., C 2002; 3: 25-52.
40. Wolfbeis OS. Anal. Chem. 2002; 74: 2663-2678.
41. Holten D, Bocian DF and Lindsey JS. Acc. Chem. Res. 2002; 35: 57-69.
42. Agbaria RA, Oldham PB, McCarroll M, McGown LB and Warner IM. Anal. Chem. 2002; 74: 3952-3962.
43. Chang CK and Abdalmuhdi I. J. Org. Chem. 1983; 48: 5388-5390.
44. Chang CK and Abdalmuhdi I. Angew. Chem., Int. Ed. 1984; 23: 164-165.
45. Eaton SS, Eaton GR and Chang CK. J. Am. Chem. Soc. 1985; 107: 3177-3184.
46. Collman JP, Hutchison JE, Lopez MA, Tabard A, Guilard R, Seok WK, Ibers JA and L'Her M. J. Am. Chem. Soc. 1992; 114: 9869-9877.
47. Guilard R, Lopez MA, Tabard A, Richard P, Lecomte C, Brandès S, Hutchison JE and Collman JP. J. Am. Chem. Soc. 1992; 114: 9877-9889.
48. Tardieux C. Ph.D. Thesis, University of Burgundy: Dijon, 1997.
49. Bolze F. Ph.D. Thesis, University of Burgundy: Dijon, 2001.
50. Chang CJ, Deng Y, Heyduk AF, Chang CK and Nocera DG. Inorg. Chem. 2000; 39: 959-966.
51. Deng Y, Chang CJ and Nocera DG. J. Am. Chem. Soc. 2000; 122: 410-411.
52. Bolze F, Gros CP, Drouin M, Espinosa E, Harvey PD and Guilard R. J. Organomet. Chem. 2002; 643-644: 89-97.
53. Faure S, Stern C, Guilard R and Harvey PD. J. Am. Chem. Soc. 2004; 126: 1253-1261.
54. Strachan J-P, Gentemann S, Seth J, Kalsbeck WA, Lindsey JS, Holten D and Bocian DF. J. Am. Chem. Soc. 1997; 119: 11191-11201.
55. Collman JP, Chng LL and Tyvoll DA. Inorg. Chem. 1995; 34: 1311-1324.
56. Collman JP, Fish HT, Wagenknecht PS, Tyvoll DA, Chng L-L, Eberspacher TA, Brauman JI, Bacon JW and Pignolet LH. Inorg. Chem. 1996; 35: 6746-6754.
57. Hutchison JE, Postlethwaite TA, Chen CH, Hathcock KW, Ingram RS, Ou W, Linton RW, Murray RW, Tyvoll DA, Chng LL and Collman JP. Langmuir 1997; 13: 2143-2148.
58. Lindsey JS, Schreiman IC, Hsu HC, Kearney PC and Marguerettaz AM. J. Org. Chem. 1987; 52: 827-836.
59. Naruta Y, Sasayama M and Sasaki T. Angew. Chem., Int. Ed. 1994; 33: 1839-1841.
60. Faure S, Stern C, Guilard R and Harvey PD. Manuscript in preparation.
61. Lee CH and Lindsey JS. Tetrahedron 1994; 50: 11427-11440.
62. Rao PD, Dhanalekshmi S, Littler BJ and Lindsey JS. J. Org. Chem. 2000; 65: 7323-7344.
63. Li FR, Yang KX, Tyhonas JS, MacCrum KA and Lindsey JS. Tetrahedron 1997; 53: 12339-12360.
64. Littler BJ, Ciringh Y and Lindsey JS. J. Org. Chem. 1999; 64: 2864-2872.
65. Geier III GR, Riggs JA and Lindsey JS. J. Porphyrins Phthalocyanines 2001; 5: 681-690.
66. Geier GR, Littler BJ and Lindsey JS. J. Chem. Soc., Perkin Trans. 2 2001: 712-718.
67. Geier III GR, Callinan JB, Rao PD and Lindsey JS. J. Porphyrins Phthalocyanines 2001; 5: 810-823.
68. Lee C-H, Li F, Iwamoto K, Dadok J, Bothner-By AA and Lindsey JS. Tetrahedron 1995; 51: 11645-11672.
69. Cho W-S, Kim H-J, Littler BJ, Miller MA, Lee C-H and Lindsey JS. J. Org. Chem. 1999; 64 (21): 7890-7901.
70. Barbero M, Cadamuro S, Degani I, Fochi R, Gatti A and Regondi V. Synthesis 1986: 1074-1076.
71. Barbero M, Cadamuro S, Degani I, Flochi R, Gatti A and Regondi V. J. Org. Chem. 1988; 53: 2245-2250.
72. Jérôme F, Gros CP, Tardieux C, Barbe JM and Guilard R. Chem. Commun. (Cambridge, U. K.) 1998: 2007-2008.
73. Kadish KM, Ou ZP, Shao JG, Gros CP, Barbe JM, Jérôme F, Bolze F, Burdet F and Guilard R. Inorg. Chem. 2002; 41: 3990-4005.
74. Brückner C, Barta CA, Brinas RP and Bauer JAK. Inorg. Chem. 2003; 42: 1673-1680.
75. 2Co stand for porphyrin free-base and cobalt corrole.