One-pot preparation of [n]Ladderanes by [2π + 2π] photocycloaddition

European Journal of Organic Chemistry

Volumn , Issue 3, 2005, Pages 567-581

  Hopf, Henning ^a   Greiving, Helmut ^a   Beck, Christian ^b   Dix, Ina ^a   Jones, Peter G ^a   Desvergne, Jean Pierre ^c   Bouas Laurent, Henri ^c  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b KPMG AG   (Germany)

^c UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

2 + 2 photocycloaddition; n Ladderanes; Cinnamate vinylogs; Cyclophanes

Indexed keywords

1,3 BUTADIENE DERIVATIVE; [3]LADDERANE DERIVATIVE; [5]LADDERANE DERIVATIVE; ALICYCLIC COMPOUND; CINNAMIC ACID DERIVATIVE; CINNAMOPHANE DERIVATIVE; CYCLOBUTANE DERIVATIVE; PARACYCLOPHANE DERIVATIVE; POLYENE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL STRUCTURE; COLOR; CYCLIZATION; CYCLOADDITION; HORNER REACTION; PHOTOCHEMISTRY; PHOTOCYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 14344251625     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400596     Document Type: Article

References (47)

1. H. Greiving, H. Hopf, P. G. Jones, P. Bubenitschek, J. P. Desvergne, H. Bouas-Laurent, Eur. J. Org. Chem. 2005, 558-566, preceding paper.
2. H. Greiving, H. Hopf, P. G. Jones, P. Bubenitschek, J. P. Desvergne, H. Bouas-Laurent, Liebigs Ann. 1995, 1949-1956.
3. a) R. Criegee, Angew. Chem. 1962, 74, 703-712; Angew. Chem. Int. Ed. Engl. 1962, 1, 519-527;
4. a) R. Criegee, Angew. Chem. 1962, 74, 703-712; Angew. Chem. Int. Ed. Engl. 1962, 1, 519-527;
5. b) G. Mehta, M. B. Viswanath, G. N. Sastry, E. G. Jemmis, D. S. K. Reddy, A. C. Kunwar, Angew. Chem. 1992, 104, 1557-1558; Angew. Chem. Int. Ed. Engl. 1992, 31, 1488-1490;
6. b) G. Mehta, M. B. Viswanath, G. N. Sastry, E. G. Jemmis, D. S. K. Reddy, A. C. Kunwar, Angew. Chem. 1992, 104, 1557-1558; Angew. Chem. Int. Ed. Engl. 1992, 31, 1488-1490;
7. c) G. Mehta, M. B. Viswanath, M. Nethaji, K. Venkatesan, J. Chem. Soc., Chem. Commun. 1992, 82-84. For a recent highlight on ladderanes see: H. Hopf, Angew. Chem. 2003, 115, 2928-2931; Angew. Chem. Int. Ed. 2003, 42, 2822-2825. For other recent original contributions see: Y. Okada, M. Kaneko, J. Nishimura, Tetrahedron Lett. 2001, 42, 1919-1921; Y. Gao, T. Friščić, L. R. MacGillivray, Angew. Chem. 2004, 116, 234-238; Angew. Chem. Int. Ed. 2004, 43, 232-236.
8. c) G. Mehta, M. B. Viswanath, M. Nethaji, K. Venkatesan, J. Chem. Soc., Chem. Commun. 1992, 82-84. For a recent highlight on ladderanes see: H. Hopf, Angew. Chem. 2003, 115, 2928-2931; Angew. Chem. Int. Ed. 2003, 42, 2822-2825. For other recent original contributions see: Y. Okada, M. Kaneko, J. Nishimura, Tetrahedron Lett. 2001, 42, 1919-1921; Y. Gao, T. Friščić, L. R. MacGillivray, Angew. Chem. 2004, 116, 234-238; Angew. Chem. Int. Ed. 2004, 43, 232-236.
9. c) G. Mehta, M. B. Viswanath, M. Nethaji, K. Venkatesan, J. Chem. Soc., Chem. Commun. 1992, 82-84. For a recent highlight on ladderanes see: H. Hopf, Angew. Chem. 2003, 115, 2928-2931; Angew. Chem. Int. Ed. 2003, 42, 2822-2825. For other recent original contributions see: Y. Okada, M. Kaneko, J. Nishimura, Tetrahedron Lett. 2001, 42, 1919-1921; Y. Gao, T. Friščić, L. R. MacGillivray, Angew. Chem. 2004, 116, 234-238; Angew. Chem. Int. Ed. 2004, 43, 232-236.
10. c) G. Mehta, M. B. Viswanath, M. Nethaji, K. Venkatesan, J. Chem. Soc., Chem. Commun. 1992, 82-84. For a recent highlight on ladderanes see: H. Hopf, Angew. Chem. 2003, 115, 2928-2931; Angew. Chem. Int. Ed. 2003, 42, 2822-2825. For other recent original contributions see: Y. Okada, M. Kaneko, J. Nishimura, Tetrahedron Lett. 2001, 42, 1919-1921; Y. Gao, T. Friščić, L. R. MacGillivray, Angew. Chem. 2004, 116, 234-238; Angew. Chem. Int. Ed. 2004, 43, 232-236.
11. c) G. Mehta, M. B. Viswanath, M. Nethaji, K. Venkatesan, J. Chem. Soc., Chem. Commun. 1992, 82-84. For a recent highlight on ladderanes see: H. Hopf, Angew. Chem. 2003, 115, 2928-2931; Angew. Chem. Int. Ed. 2003, 42, 2822-2825. For other recent original contributions see: Y. Okada, M. Kaneko, J. Nishimura, Tetrahedron Lett. 2001, 42, 1919-1921; Y. Gao, T. Friščić, L. R. MacGillivray, Angew. Chem. 2004, 116, 234-238; Angew. Chem. Int. Ed. 2004, 43, 232-236.
12. c) G. Mehta, M. B. Viswanath, M. Nethaji, K. Venkatesan, J. Chem. Soc., Chem. Commun. 1992, 82-84. For a recent highlight on ladderanes see: H. Hopf, Angew. Chem. 2003, 115, 2928-2931; Angew. Chem. Int. Ed. 2003, 42, 2822-2825. For other recent original contributions see: Y. Okada, M. Kaneko, J. Nishimura, Tetrahedron Lett. 2001, 42, 1919-1921; Y. Gao, T. Friščić, L. R. MacGillivray, Angew. Chem. 2004, 116, 234-238; Angew. Chem. Int. Ed. 2004, 43, 232-236.
13. H. Hopf, Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000, chapter 15-3, and references therein.
14. a) J. Kaszynski, J. Michl, J. Am. Chem. Soc. 1988, 110, 5225-5226;
15. b) H. E. Zimmerman, T. D. Goldman, T. K. Hirzel, S. P. Schmidt, J. Org. Chem. 1980, 45, 3933-3951.
16. P. E. Eaton, K. Pramod, E. R. Gilardi, J. Am. Chem. Soc. 1999. 121, 4111-4123.
17. G. R. Newkome, X. Lin, C. Yaiong, G. H. Escamilla, J. Org. Chem. 1993, 58, 3123-3129 and references cited therein.
18. G. Mehta, M. B. Viswanath, A. C. Kunwar, J. Org. Chem. 1994, 59, 6131-6132.
19. R. N. Warrener, G. Abbenante, J. Am. Chem. Soc. 1994, 116, 3645-3646 and references cited therein.
20. W. Li, M. A. Fox, J. Am. Chem. Soc. 1996, 118, 11752-11758.
21. J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik, M. S. M. Jetten, Nature 2002, 419, 708-712.
22. K. Takahashi, Y. Mazaki, K. Kobayashi, J. Chem. Soc. Chem. Commun. 1996, 2275-2276.
23. S. Ayyapan, X. Bu, A. K. Cheetham, S. Natarajan, C. N. R. Rao, J. Chem. Soc. Chem. Commun. 1998, 2181-2182.
24. J. S. Silverman, C. D. Abernethy, R. A. Jones, A. H. Cowley, J. Chem. Soc. Chem. Commun. 1999, 1645-1646.
25. H. Hopf, H. Greiving, P. G. Jones, P. Bubenitschek, Angew. Chem. 1995, 707, 742-744; Angew. Chem. Int. Ed. Engl. 1995, 34, 685-687.
26. H. Hopf, H. Greiving, P. G. Jones, P. Bubenitschek, Angew. Chem. 1995, 707, 742-744; Angew. Chem. Int. Ed. Engl. 1995, 34, 685-687.
27. a) H. Hopf, Angew. Chem. 1972, 84, 471-472: Angew. Chem. Int. Ed. Engl. 1972, 77, 419-420;
28. a) H. Hopf, Angew. Chem. 1972, 84, 471-472: Angew. Chem. Int. Ed. Engl. 1972, 77, 419-420;
29. b) H. Hopf, I. Böhm, J. Kleinschroth, Org. Synth. 1981, 60, 41-48.
30. a) A. Rieche, H. Gross, E. Höft, Chem. Ber. 1960, 93, 88-94;
31. b) M. Psiorz, R. Schmidt, Chem. Ber. 1987, 120, 1825-1828;
32. H. Zitt, I. Dix, H. Hopf, P. G. Jones, Eur. J. Org. Chem. 2002, 2298-2307.
33. a) D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4156-4158;
34. b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287.
35. a) H. H. Jaffé, M. Orchin, Theory and Applications of Ultraviolet Spectroscopy, John Wiley & Sons, New York, 1965, pp. 196-241;
36. b) D. H. Williams, I. Fleming, Spectroscopic Methods in Organic Chemistry, McGraw-Hill, London, 1966, pp. 24-26.
37. B. S. Green, M. Lahav, G. M. J. Schmidt, J. Chem. Soc. [B] 1971, 1552-1564.
38. J. C. Calvert, J. N. Pǐtts, Photochemistry, John Wiley & Sons, New York, 1966, pp. 728-747.
39. a) H. Bouas-Laurent, H. Dürr, Pure Appl. Chem. 2001, 73, 639-665;
40. b) Photochromism, Molecules and Systems, (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam, 2003, revised edition.
41. a) H. Hopf, Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000, pp. 323-330;
42. b) M. S. Newman, D. Lednicer, J. Am. Chem. Soc. 1956, 78, 4765-4770;
43. c) R. H. Martin, Angew. Chem. 1974, 86, 727-738; Angew. Chem. Int. Ed. Engl. 1974, 13, 649-660.
44. c) R. H. Martin, Angew. Chem. 1974, 86, 727-738; Angew. Chem. Int. Ed. Engl. 1974, 13, 649-660.
45. T. M. Cresp, M. V. Sargent, P. Vogel, J. Chem. Soc. Perkin Trans, 1 1974, 37-41.
46. E. A. Truesdale, Ph. D. Dissertation, UCLA, Los Angeles, 1973.
47. K. Broschinski, Ph. D. Dissertation, Technische Universität Braunschweig, Braunschweig, 1984.