Novel oxidation reactions of sterically demanding 3,6-di-tert-butyl porphyrin-o-quinones to muconic anhydride derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 20, 1997, Pages 2589-2592

  Speck, Marcus ^a   Senge, Mathias O ^a   Schäfer, Andreas ^a   Kurreck, Harry ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ELECTRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS;

EID: 0030663106     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10027-0     Document Type: Article

References (16)

1. (a) Kurreck, H.; Huber, M. Angew. Chem. Int. Ed. Engl. 1995, 34, 849.
2. (b) Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
3. (a) Jang, H. G; Cox, D. D.; Que, L., Jr. J. Am. Chem. Soc. 1991, 113, 9200.
4. (b) Funabiki, T.; Ishikawa, M.; Nagai, Y.; Yorita, J.; Yoshida, S.; J. Chem. Soc., Chem. Commun. 1994, 1951.
5. (c) Koch, W. O.; Krueger, H.-J. Angew. Chem. Int Ed. Engl. 1996, 34, 2671.
6. (d) Bianchini, C.; Frediani, P.; Laschi, F.; Meli, A.; Vizza, F.; Zanello, P. Inorg. Chem. 1990, 29, 3402.
7. (e) Matsuura, T.; Matsushima, H.; Kato, S.; Saito, I. Tetrahedron 1972, 28, 5119.
8. Belostotskaya, I. S.; Komissarova, N. L.; Dzhuaryan, E. V.; Ershov, V. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 1594.
9. 1 (I>2σ(I)) = 0.0480, wR2 (all data) = 0.1248.
10. (b) Complete data have been deposited with the CCDC.
11. Rieche, A.; Gross, H.; Höft, E. Chem. Ber. 1960, 93, 88.
12. Lindsey, J. S.; Schreiman, L. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827.
13. Lindsey, J. S.; Wagner, R. W. J. Org. Chem. 1987, 54, 828.
14. 4b
15. Speier, G.; Tyeklar, Z. Chem. Ber. 1979, 112, 389.
16. 13C NMR: (126 MHz) δ 213.42, 205.30, 156.85, 141.91, 141.62, 135.72, 134.46, 127.90, 126.78, 126.73, 126.70, 121.51, 120.83, 113.05, 45.67, 43.71, 27.08, 26.33 ppm; HRMS: calc. 732.34643, found 732.34621; mp 248-50 °C.