Conversion of mono- and tetra-thiacalix[4]arenes to sulfilimine derivatives and unexpected formation of monospirodienone derivatives

Heterocyclic Communications

Volumn 11, Issue 3-4, 2005, Pages 249-254

  Morohashi, Naoya ^a   Kojima, Makoto ^a   Suzuki, Akihiro ^a   Ohba, Yoshihiro ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23644439903     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2005.11.3-4.249     Document Type: Article

References (28)

1. For books on calixarenes see: a) C. D. Gutsche, In Calixarenes revisited. Monographs in supramolecular chemistry; J. F. Stoddart, Ed.; The Royal Society of Chemistry: Cambridge, 6 (1998).
2. b) In Calixarenes (2001); Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens, Eds.; Kluwer Academic: Dordrecht (2001).
3. In Calixarenes in action; L. Mandolini, R. Ungaro, Eds.; Imperial College: London (2000).
4. a) K. Ito, A. Kida, Y. Ohba, and T. Sone, Chem. Lett. (1998), 1221.
5. b) K. Ito, Y. Ohba, and T. Sone, Nippon Kagaku Kaishi 217 (1999).
6. T. Sone, Y. Ohba, K. Moriya, and K. Ito, Tetrahedron, 53, 10689 (1997).
7. H. Kumagai, M. Hasegawa, S. Miyanari, Y. Sugawa, Y. Sato, T. Hori, S. Ueda, H. Kamiyama, and S. Miyano, Tetrahedron Lett. 38, 3971 (1997).
8. N. Iki, and S. Miyano, J. Inclu. Phenom. Macrocycl. Chem. 41, 99 (2001).
9. b) N. Iki, and S. Miyano, Nippon Kagaku Kaishi, 609 (2001).
10. c) N. Morohashi, N. Iki, and S. Miyano, Yuki Gosei Kagaku Kyokaishi, 60, 550 (2002);
11. Chem. Abstr. 136, 452024 (2002).
12. a) G. Mislin, E. Graf, M. W. Hosseini, A. D. Cian, and J. Fisher, Chem. Commun. 1345 (1998).
13. b) G. Mislin, E. Graf, M. W. Hosseini, A. D. Cian, and J. Fisher, Tetrahedron Lett., 40, 1129 (1999).
14. c) N. Morohashi, N. Iki, A. Sugawara, S. Miyano, Tetarahedron, 57, 5557 (2001).
15. d) N. Morohashi, H. Katagiri, N. Iki, Y. Yamane, C. Kabuto, T. Hattori, and S. Miyano, J. Org. Chem., 68, 2324 (2003).
16. For example: a) K. Tshujihara, N. Furukawa, K. Oae, and S. Oae, Bull. Chem. Soc. Jpn. 42, 2631 (1969).
17. b) A. L. Marzinzik, and K. B. Sharpless, J. Org. Chem. 66, 594 (2001).
18. c) Johnson, C. R. In Comprehensive Organic Chemistry, Vol 3;
19. Barton, D. H. R; Ollis, W. D., Eds.; Pergamon: New York, Chap. 11.10, 215 (1979).
20. +).
21. For example: S. E. Biali, Synlett., 1 (2003).
22. Actually, treatment of I with chloramine T gave the corresponding monospirodienone in 64 % isolated yield.
23. +).
24. Spectral data of compound 7, see: N. Morohashi, N. Iki, T. Onodera, C. Kabuto, and S. Miyano, Tetrahedron Lett., 41, 5093 (2000).
25. +).
26. +).
27. +).
28. int = 0.052), 2939 observed reflections (I >3.00σ(I)), 540 parameters, R = 0.070, wR = 0.073, refined against |F|, GOF = 0.987. Crystallographic data for this crystal has been deposited with the Cambridge Crystallographic Date Centre as supplementary publication no. CCDC 258069. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK.