Complete assignment of the 1H and 13C NMR and conformational of bonellin dimethyl ester

Journal of Porphyrins and Phthalocyanines

Volumn 8, Issue 12, 2004, Pages 1376-1382

  Hynninen, Paavo H ^a   Helaja, Juho ^a   Montforts, Franz Peter ^b   Müller, Claudia M ^b  

^a UNIVERSITY OF HELSINKI   (Finland)

^b UNIVERSITY OF BREMEN   (Germany)

Author keywords

Aromaticity; Bonellin; Chlorin; Nuclear magnetic resonance; Photodynamic therapy; Porphyrin; Stereochemistry

Indexed keywords

ANHYDROBONELLIN; ANNULENE DERIVATIVE; BONELLIN; BONELLIN DIMETHYL ESTER; CHLORIN; PORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; CYCLIZATION; FRIEDEL CRAFTS REACTION; PHOTODYNAMIC THERAPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 14744294611     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/s1088424604000738     Document Type: Article

References (38)

1. Montforts F-P, Gerlach B and Höper F. Chem. Rev. 1994; 94: 327-347.
2. Kräutler B. Chimia 1987; 41: 277-292.
3. Hynninen PH. In Chlorophylls, ed. Scheer H. CRC Press: Boca Raton, 1991; 145-209.
4. Fischer H and Stern A. Die Chemie des Pyrrols, II. Band/2. Hälfte. Akademische Verlagsgesellschaft: Leipzig, 1940; 138.
5. Agius L, Ballantine JA, Ferrito V, Jaccarini V, Murray-Rust P, Pelter A, Psaila AF and Schembri PJ. Pure Appl. Chem. 1979; 51: 1847-1864.
6. Ballantine JA, Psaila AF, Pelter A, Murray-Rust P, Ferrito V, Schembri P and Jaccarini V. J. Chem. Soc. Perkin Trans, 1. 1980; 1080-1089.
7. Lederer E. Compt. rend. Acad. Sei. Paris 1939; 209: 528-530.
8. Pelter A, Ballantine JA, Murray-Rust P, Ferrito V and Psaila AF. Tetrahedron Lett. 1978; 1881-1984.
9. Montforts F-P, Müller CM and Lincke A. Liebigs Ann. Chem. 1990; 415-418.
10. Battersby AR, Dutton CJ and Fookes CJR. J. Chem. Soc. Perkin Trans, 1. 1988; 1569-1576.
11. Montforts F-P and Schwartz UM. Liebigs Ann. Chem. 1991; 709-725.
12. Nigrelli RF, Stempien MF, Ruggieri GD, Liguori VR and Cecil JT. Fed. Proc. Fed. Am. Soc. Exp. Biol. 1967; 26: 1197-1205.
13. Nyman ES and Hynninen PH. J. Photochem. Photobiol. B: Biology 2004; 73: 1-28.
14. Smith KM, Goff DA and Abraham RJ. J. Org. Chem. 1987; 52: 176-180.
15. Helaja J, Tauber AY, Kilpeläinen I and Hynninen PH. Magn. Reson. Chem. 1997; 35: 619-628.
16. Hyvärinen K, Helaja J, Kuronen P, Kilpeläinen I and Hynninen PH. Magn. Reson. Chem. 1995; 33: 646-656.
17. Helaja J, Hyvärinen K, Heikkinen S, Kilpeläinen I and Hynninen PH. J. Mol. Struct. 1995; 354: 71-79.
18. Kilpeläinen I, Kaltia S, Kuronen P, Hyvärinen K and Hynninen PH. Magn. Reson. Chem. 1994; 32: 29-35.
19. Helaja J, Montforts F-P, Kilpeläinen I and Hynninen PH. J. Org. Chem. 1999; 64: 432-437.
20. Helaja J, Stapelbroek-Möllmann M, Kilpeläinen I and Hynninen PH. J. Org. Chem. 2000; 65: 3700-3707.
21. Summers MF, Marzilli LG and Bax A. J. Am. Chem. Soc. 1986; 108: 4285-4294.
22. Bothner-By AA, Stephens RL, Lee J, Warren CD and Jeanloz RW. J. Am. Chem. Soc. 1984; 106: 811-813.
23. Laatikainen RJ. J. Magn. Reson. 1991; 92: 1-9.
24. Laatikainen RJ, Niemitz M and Sundelin J. ©1993-94 PERCH Project, University of Kuopio, Department of Chemistry, PO Box 1627, FIN-70211 Kuopio, Finland.
25. Barfield M, Spear RJ and Sternhell S. Chem. Rev. 1976; 76: 593-624.
26. Clezy PS, Fookes CJR and Sternhell S. Aust. J. Chem. 1978; 31: 639-648.
27. Lötjönen S and Hynninen PH. Org. Magn. Reson. 1984; 22: 510-514.
28. Crossley MJ, Harding MM and Sternhell S. J. Am. Chem. Soc. 1986; 108: 3608-3613.
29. Crossley MJ, Field LD, Harding MM and Sternhell S. J. Am. Chem. Soc. 1987; 109: 2335-2341.
30. Crossley MJ, Harding MM and Sternhell S. J. Org. Chem. 1988; 53: 1132-1137.
31. Crossley MJ, Harding MM and Sternhell S. J. Am. Chem. Soc. 1992; 114: 3266-3272.
32. Crossley MJ, Harding MM and Sternhell S. J. Org. Chem. 1992; 57: 1833-1837.
33. Schlabach M, Scherer G and Limbach H-H. J. Am. Chem. Soc. 1991; 113: 3550-3558.
34. rd revised edn). Wiley-VCH: Weinheim, 1998; 276-279.
35. nd edn). John Wiley & Sons: Chichester, 1995; 397-408.
36. nd edn). VCH Publishers: New York, 1994; 327-343.
37. Abraham RJ, Pople JA and Bernstein HJ. Can. J. Chem. 1958; 36: 1302-1307.
38. Abraham RJ and Bernstein HJ. Can. J. Chem. 1961; 39: 216-230.