Synthesis of Bronzaphyrin NS

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1168-1172

  Johnson, Martin R ^a,b  

^a GEORGE WASHINGTON UNIVERSITY   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006110525     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961849u     Document Type: Article

References (25)

1. Sessler, J. L. Angew. Chem., Int. Ed. Engl. 1994, 33, 1348-1350.
2. (a) Sessler, J. L.; Burrell, A. K. Top. Curr. Chem. 1991, 161, 177-273.
3. (b) Vogel, E. Pure Appl. Chem. 1993, 65, 143-152.
4. (c) Sapphyrin review: Sessler, J. L.; Cyr, M.; Burrell, A. K. Tetrahedron 1992, 48, 9661-9672.
5. 4b and, therefore, "pentaplanar".
6. Thiophene-containing annulenes: (a) Kozaki, M.; Parakka, J. P.; Cava, M. P. J. Org. Chem. 1996, 61, 3657-3661. (b) Hu, Z.; Atwood, J. L.; Cava, M. P. J. Org. Chem. 1994, 59, 8071-8075. (c) Hu, Z. Y.; Cava, M. P. Tetrahedron Lett. 1994, 35, 3493-3496. (d) Hu, Z.; Scordilis-Kelley, C.; Cava, M. P. Tetrahedron Lett. 1993, 34, 1879-1882. (e) Elinger, F.; Gieren, A.; Hübner, Th.; Lex, J.; Merz, A.; Neidlein, R.; Salbeck, J. Monatsh. Chem. 1993, 124, 931-943.
7. Thiophene-containing annulenes: (a) Kozaki, M.; Parakka, J. P.; Cava, M. P. J. Org. Chem. 1996, 61, 3657-3661. (b) Hu, Z.; Atwood, J. L.; Cava, M. P. J. Org. Chem. 1994, 59, 8071-8075. (c) Hu, Z. Y.; Cava, M. P. Tetrahedron Lett. 1994, 35, 3493-3496. (d) Hu, Z.; Scordilis-Kelley, C.; Cava, M. P. Tetrahedron Lett. 1993, 34, 1879-1882. (e) Elinger, F.; Gieren, A.; Hübner, Th.; Lex, J.; Merz, A.; Neidlein, R.; Salbeck, J. Monatsh. Chem. 1993, 124, 931-943.
8. Thiophene-containing annulenes: (a) Kozaki, M.; Parakka, J. P.; Cava, M. P. J. Org. Chem. 1996, 61, 3657-3661. (b) Hu, Z.; Atwood, J. L.; Cava, M. P. J. Org. Chem. 1994, 59, 8071-8075. (c) Hu, Z. Y.; Cava, M. P. Tetrahedron Lett. 1994, 35, 3493-3496. (d) Hu, Z.; Scordilis-Kelley, C.; Cava, M. P. Tetrahedron Lett. 1993, 34, 1879-1882. (e) Elinger, F.; Gieren, A.; Hübner, Th.; Lex, J.; Merz, A.; Neidlein, R.; Salbeck, J. Monatsh. Chem. 1993, 124, 931-943.
9. Thiophene-containing annulenes: (a) Kozaki, M.; Parakka, J. P.; Cava, M. P. J. Org. Chem. 1996, 61, 3657-3661. (b) Hu, Z.; Atwood, J. L.; Cava, M. P. J. Org. Chem. 1994, 59, 8071-8075. (c) Hu, Z. Y.; Cava, M. P. Tetrahedron Lett. 1994, 35, 3493-3496. (d) Hu, Z.; Scordilis-Kelley, C.; Cava, M. P. Tetrahedron Lett. 1993, 34, 1879-1882. (e) Elinger, F.; Gieren, A.; Hübner, Th.; Lex, J.; Merz, A.; Neidlein, R.; Salbeck, J. Monatsh. Chem. 1993, 124, 931-943.
10. Thiophene-containing annulenes: (a) Kozaki, M.; Parakka, J. P.; Cava, M. P. J. Org. Chem. 1996, 61, 3657-3661. (b) Hu, Z.; Atwood, J. L.; Cava, M. P. J. Org. Chem. 1994, 59, 8071-8075. (c) Hu, Z. Y.; Cava, M. P. Tetrahedron Lett. 1994, 35, 3493-3496. (d) Hu, Z.; Scordilis-Kelley, C.; Cava, M. P. Tetrahedron Lett. 1993, 34, 1879-1882. (e) Elinger, F.; Gieren, A.; Hübner, Th.; Lex, J.; Merz, A.; Neidlein, R.; Salbeck, J. Monatsh. Chem. 1993, 124, 931-943.
11. (a) Miller, D. C.; Johnson, M. R.; Ibers, J. A. J. Org. Chem. 1994, 59, 2877-2879.
12. (b) Johnson, M. R.; Miller, D. C.; Bush, K.; Becker, J. J.; Ibers, J. A. J. Org. Chem. 1992, 57, 4414-4417.
13. Merrill, B.; LeGoff, E. J. Org. Chem. 1990, 112, 2810-2813.
14. Johnson, M. R. Unpublished data.
15. Meier, J. Chem. Abstr. 1993, 118, 168706.
16. (a) Benetti, S.; Romagnoli, R.; De Risi, C.; Spalluto, G.; Zanirato, V. Chem. Rev. 1995, 95, 1065-1114.
17. (b) The reaction of Meldrum's acid with acid chlorides represents an additional possible route to large-scale synthesis of β-keto esters: Oikawa, Y.; Yoshioka, T.; Sugano, K.; Yonemitsu, O. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VI, pp 359-262.
18. (c) Oikawa, Y.; Sugano, K.; Yonemitsu, O. J. Org. Chem. 1978, 43, 2087-2088.
19. 4·2THF is efficaciously handled.
20. 2, instantly gave a brilliant deep purple color that also quickly turned brown. No products were isolable from this reaction.
21. Platt, J. R. J. Chem. Phys. 1949, 17, 484-495.
22. The elemental compositions of dihydrobronzaphyrin and bronzaphyrin are within experimental error of each other and cannot be used to distinguish between the two.
23. 2 must be added and the matrix broken up into small pieces and stirred until homogenous. The reaction outcome is unaffected by these extra steps.
24. Dry ice added to the residue works well.
25. Katzenellenbogen, J. A.; Utawanit, T. J. Am. Chem. Soc. 1974, 96, 6153-6158.