Photochemical generation of cyclophanes from 1,3,5-trisubstituted benzenes with chalcone chromophores

European Journal of Organic Chemistry

Volumn , Issue 12, 2007, Pages 1983-1990

  Karpuk, Elena ^a   Schollmeyer, Dieter ^a   Meier, Herbert ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Cycloaddition; Cyclophanes; Diastereoselectivity; Photochemistry; Regioselectivity

Indexed keywords

EID: 34250633664     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700010     Document Type: Article

References (44)

1. C. J. Brown, A. C. Farthing, Nature 1949, 164, 915.
2. D. J. Cram, J. Steinberg, J. Am. Chem. Soc. 1951, 73, 5691-5704.
3. Selected books and review articles: a) Modern Cyclophane Chemistry (Eds.: R. Gleiter, H. Hopf), Wiley-VCH, Weinheim, 2004;
4. b) F. Vögtle, Cyclophane Chemistry: Synthesis Structures and Reactions, Wiley-VCH, Chichester, 1999;
5. c) F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, 1991;
6. d) P. M. Keehn, S. M. Rosenfeld, Cyclophanes, Academic Press, New York, 1983, 2 vols.;
7. e) B. König, Top. Curr. Chem. 1998, 196, 91-136;
8. f) F. Vögtle, Top. Curr. Chem. 1983, 113;
9. g) F. Vögtle, Top. Curr. Chem. 1983, 115.
10. E. Müller, H. Meier, M. Sauerbier, Chem. Ber. 1970, 103, 1356-1363.
11. See also J. Juriew, E. Merkuschew, T. Skorochodowa, W. Winter, H. Meier, Angew. Chem. 1981, 93, 285-286;
12. Angew. Chem. Int. Ed. Engl. 1981, 20, 269-270,
13. H. Meier, J. Juriew, W. Winter, J. Photochem. 1981, 17, 1272.
14. For the photochemical synthesis of cyclophanes, see for example: J. Nishimura, Y. Nakamura, Y. Hayashida, T. Kudo, Acc. Chem. Res. 2000, 33, 679-686;
15. J. Nishimura, Y. Nakamura, T. Yamazaki, S. Inokuma in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. Horspool, F. Lenci), CRC Press, Boca Raton, 2004.
16. See however M. A. Kinder, P. Margaretha, Org. Lett. 2000, 2, 4253-4255.
17. H. Meier, E. Karpouk, Tetrahedron Lett. 2004, 45, 4477-4480.
18. Due to the 1,3,5-trisubstitution, the chalcone units can be regarded in the first approximation as independent chromophores.
19. S. V. Tsukerman, E. V. Danilchenko, V. M. Nikitchenko, V. F. Lavrushin, Khim. Geterotsikl. Soedin. 1974, 1394-1397
20. [Chem. Abstr. 1975, 82, 43245u].
21. S. V. Tsukerman, E. V. Danilchenko, V. M. Nikitchenko, V. F. Lavrushin, J. Org. Chem. USSR (Engl. Transl.) 1974, 10, 2643-2644;
22. Zh. Org. Khim. 1974, 10, 2623-2624.
23. max value of 309 nm.
24. MestRe-C2.3a Software.
25. 3J(trans) couplings in the four-membered rings. However, the obtained coupling constants of 9.95 and 8.95 Hz are too similar to permit a decision between 8ab and 8ac.
26. E. Karpouk, Dissertation, Mainz, 2004.
27. V. A. Dombrovskii, L. A. Yanovskaya, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1975, 24, 2503-2504;
28. Izv. Akad. Nauk SSSR Ser. Khim. 1975, 24, 2613-2614.
29. W. Winter, U. Langjahr, H. Meier, J. Merkushew, J. Juriew, Chem. Ber. 1984, 117, 2452-2463.
30. R. Petermann, C. Schnorpfeil, M. Lehmann, M. Fetten, H. Meier, J. Inf. Rec. 2000, 25, 259-264.
31. H. Meier, M. Lehmann in Encyclopedia of Nanoscience and Nanotechnology (Ed.: H. S. Nalwa), American Scientific Publisher, Stevenson Ranch, CA, 2004, vol. 10, pp. 95-106.
32. s arrangement.
33. G. M. J. Schmidt, Pure Appl. Chem. 1971, 27, 647-678.
34. H. Stobbe, A. Hensel, Ber. Dtsch. Chem. Ges. 1926, 59, 2254-2265.
35. H. Stobbe, K. Bremer, J. Prakt. Chem. 1929, 123, 1-60.
36. F. Toda, K. Tanaka, M. Kato, J. Chem. Soc., Perkin Trans. 1 1998, 1315-1318.
37. For the first clear decision, see S. Caccamese, J. A. McMillan, G. Montaudo, J. Org. Chem. 1978, 43, 2703-2704.
38. M. Hasegawa, M. Nohara, K. Saigo, T. Mori, H. Nakanishi, Tetrahedron Lett. 1984, 25, 561-564.
39. M. Hasegawa, K. Saigo, T. Mori, H. Uno, M. Nohara, H. Nakanishi, J. Am. Chem. Soc. 1985, 107, 2788-2793.
40. For example, see: U. Meyer, N. Lahrahar, P. Marsau, H. Hopf, H. Greiving, J.-P. Desvergne, H. Bouas-Laurent, Liebigs Ann./Recueil 1997, 381-384;
41. H. Greiving, H. Hopf, P. G. Jones, P. Bubenitschek, J.-P. Desvergne, H. Bouas-Laurent, Liebigs Ann. Chem. 1995, 1949-1956.
42. The assignment is based on 2D-NMR measurements (HMQC and HMBC).
43. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.
44. G. M. Sheldrick, SHELXL-97, Program for crystal structure refinement, University of Göttingen, Germany, 1997.