Phenothiazinophanes: Synthesis, structure, and intramolecular electronic communication

Organic Letters

Volumn 10, Issue 13, 2008, Pages 2797-2800

  Memminger, Karin ^a,b   Oeser, Thomas ^b   Müller, Thomas J J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 58149202958     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800920d     Document Type: Article

References (48)

1. For an excellent recent monography, see, e.g.: Modern Cyclophane Chemistry; Gleiter, R., Hopf, H., Eds.; Wiley-VCH: Weinheim, 2004.
2. For a recent review, see, e.g.: Tsuji, T. In Modern Cyclophane Chemistry; Gleiter, R., Hopf, H., Eds.; Wiley-VCH: Weinheim, 2004; pp 81-104..
3. (a) Morisaki, Y.; Chujo, Y. Angew. Chem., Int. Ed. 2006, 45, 6430-6437.
4. (b) Morisaki, Y.; Ishida, T.; Chujo, Y. Macromolecules 2002, 35, 7872-7877.
5. Sainsbury, M. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 3, p 995.
6. For cyclovoltammetric and spectroscopic data of phenothiazine, see, e.g.: (a) Tinker, L. A.; Bard, A. J. J. Am. Chem. Soc. 1979, 101, 2316-2319.
7. (b) Padusek, B.; Kalinowski, M. K. Electrochim. Acta 1983, 28, 639.
8. (c) McIntyre, R.; Gerischer, H. Ber. Bunsen Ges. Phys. Chem. 1984, 88, 963-969.
9. (a) Duesing, R.; Tapolsky, G.; Meyer, T. J. J. Am. Chem. Soc. 1990, 112, 5378-5379.
10. (b) Jones, W. E., Jr.; Chen, P.; Meyer, T. J. J. Am. Chem. Soc. 1992, 114, 387-388.
11. (c) Brun, A. M.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1991, 113, 8657-8663.
12. (d) Burrows, H. D.; Kemp, T. J.; Welburn, M. J. J. Chem. Soc., Perkin Trans. 2 1973, 969-974.
13. (e) Collin, J.-P.; Guillerez, S.; Sauvage, J.-P. J. Chem. Soc., Chem. Commun. 1989, 776-778.
14. (f) Daub, J.; Engl, R.; Kurzawa, J.; Miller, S. E.; Schneider, S.; Stockmann, A.; Wasielewski, M. R. J. Phys. Chem. A 2001, 105, 5655-5665.
15. (a) Wheland, R. C.; Gillson, J. L. J. Am. Chem. Soc. 1976, 98, 3916-3925.
16. (b) Berges, P.; Kudnig, J.; Klar, G.; Sanchez-Martinez, E.; Diaz-Calleja, R. Synth. Met. 1992, 46, 207-219.
17. (c) Knorr, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2664-2666.
18. (d) Spreitzer, H.; Scholz, M.; Gescheidt, G.; Daub, J. Liebigs Ann. Chem. 1996, 2069-2077.
19. (e) Spreitzer, H.; Daub, J. Chem.-Eur. J. 1996, 2, 1150-1158.
20. (a) Müller, T. J. J. Tetrahedron Lett. 1999, 40, 6563-6566.
21. (b) Krämer, C. S.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2000, 2, 3723-3726.
22. (c) Krämer, C. S.; Müller, T. J. J. Eur. J. Org. Chem. 2003, 3534-3548.
23. (d) Sailer, M.; Franz, A. W.; Müller, T. J. J. Chem.-Eur. J. 2008, 8, 2602-2614.
24. (a) Sailer, M.; Nonnenmacher, M.; Oeser, T.; Müller, T. J. J. Eur. J. Org. Chem. 2006, 423-435.
25. (b) Sailer, M.; Rominger, F.; Müller, T. J. J. J. Organomet. Chem. 2006, 691, 299-308.
26. (c) Hauck, M.; Schönhaber, J.; Zucchero, A. J.; Hardcastle, K. I.; Müller, T. J. J.; Bunz, U. H. F. J. Org. Chem. 2007, 72, 6714-6725.
27. (a) Krämer, C. S.; Zeitler, K.; Müller, T. J. J. Tetrahedron Lett. 2001, 42, 8619-8624.
28. (b) Krämer, C. S.; Zimmermann, T. J.; Sailer, M.; Müller, T. J. J. Synthesis 2002, 1163-1170.
29. (c) Franz, A. W.; Müller, T. J. J. Synthesis 2008, 1121-1125.
30. Grave, C.; Schlüter, A. D. Eur. J. Org. Chem. 2002, 3075-3098.
31. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 685260 (1), CCDC685261 (4a), and CCDC 685262 (6). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk).
32. For reviews, see, e.g.: (a) McMurry, J. E. Chem. Rev. 1989, 89, 1513-1524.
33. (b) Rieke, R. D.; Kim, S.-H. J. Org. Chem. 1998, 63, 5235-5239.
34. (a) Ephritikhine, M.; Villiers, C. Modern Carbonyl Olefination; Wiley-VCH Verlag GmbH: Weinheim, New York, Chichester, Brisbane, Singapore, Toronto; 1. Auflage 2004, 223-285.
35. (b) Kawase, T.; Ueda, N.; Tanake, K.; Seirai, Y.; Oda, M. Tetrahedron Lett. 2001, 42, 5509-5511.
36. (c) Vogel, E.; Binsack, B.; Hellwig, Y.; Erben, C.; Heger, A.; Lex, J.; Wu, Y. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2612-2615.
37. For the first phenothiazinophane, see: (a) Petry, C.; Lang, M.; Staab, H. A.; Bauer, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1711-1714.
38. (b) Independently from our studies, a related phenothiazinophane has just recently been reported. See: Rajakumar, P.; Kanagalatha, R. Tetrahedron Lett. 2007, 48, 8496-8500.
39. Lenoir, D. Synthesis 1977, 553-554.
40. Fürstner, A.; Bogdanović, B. Angew. Chem., Int Ed. 1996, 35, 2442-2469.
41. f = 0.78) as standards. For a reference, see: Du, H.; Fuh, R. A.; Li, J.; Corkan, A.; Lindsey, J. S. Photochem. Photobiol. 1998, 68, 141-142.
42. As implemented in: PC Spartan 02; Wavefunction Inc.: Irvine, CA, 2002.
43. (a) Robin, M. B.; Day, P. Adv. Inorg. Chem. Radiochem. 1967, 247-422.
44. (b) Bott, A. W. Curr. Sep. 1997, 61-66.
45. (c) Stoll, M. E.; Lovelace, S. R.; Geiger, W. E.; Schimanke, H.; Hyla-Kryspin, I.; Gleiter, R. J. Am. Chem. Soc. 1999, 121, 9343-9351.
46. Facchetti, A.; Mushrush, M.; Yoon, M.-H.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13859-13874.
47. Sun, D.; Rosokha, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 1388-1401.
48. Song, Y.; Di, C.; Yang, X.; Li, S.; Xu, W.; Liu, Y.; Yang, L.; Shuai, Z.; Zhang, D.; Zhu, D. J. Am. Chem. Soc. 2006, 128, 15940-15941.