MacDonald [2 + 2]-type condensation with vicinal diketones: Synthesis and properties of novel spiro-tricyclic porphodimethenes

Organic Letters

Volumn 3, Issue 15, 2001, Pages 2281-2284

  Harmjanz, Michael ^a   Božidarević, Ivana ^a   Scott, Michael J ^a  

^a University of Florida ^*  (United States)

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[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 18044404482     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016046u     Document Type: Article

References (14)

1. Da Silva, C.; Bonomo, L.; Solari, E.; Scopelliti, R.; Floriani, C.; Re, N. Chem. Eur. J. 2000, 6, 4518-4531 and references therein.
2. (a) Senge, M. O.; Runge, S.; Speck, M.; Ruhlandt-Senge, K. Tetrahedron 2000, 56, 8927-8932.
3. (b) Botulinski, A.; Buchler, J. W.; Lay, K.-L.; Stoppa, H. Liebigs Ann. Chem. 1984, 1259-1269 and references therein.
4. (a) Harmjanz, M.; Scott, M. J. Chem. Commun. 2000, 397-398.
5. (b) Harmjanz, M.; Gill, H. S.; Scott, M. J. J. Org. Chem. In press.
6. Král, V.; Sessler, J. L.; Zimmerman, R. S.; Seidel, D.; Lynch, V.; Andrioletti, B. Angew. Chem., Int. Ed. 2000, 39, 1055-1058.
7. Harmjanz, M.; Gill, H. S.; Scott, M. J. J. Am. Chem. Soc. 2000, 122, 10476-10477.
8. Harmjanz, M.; Scott, M. J. Inorg. Chem. 2000, 39, 5428-5429.
9. Lindsey, J. S.; Wagner, R. W. J. Org. Chem. 1989, 54, 828-836.
10. Young, E. R. R.; Funk, R. L. J. Org. Chem. 1998, 63, 9995-9996.
11. The crystal structures of both 1 and 2 were solved to confirm the orientation of the aceanthrenone groups. Only 1 was fully refined, and the structure is presented in the Supporting Information.
12. Takahashi, K.; Goda, T.; Yamaguchi, T.; Komura, T.; Murata, K. J. Phys. Chem. B 1999, 103, 4868-4875.
13. 3 produced crystals suitable for X-ray crystallography.
14. The hydroxymethyl groups were disordered in the solid state, and the groups were refined in two distinct orientations (60 and 40% site occupancy respectively). For clarity, only one position is shown.