Synthesis of the first examples of p-bromodienone and transannular spirodienone calixarene derivatives

Tetrahedron Letters

Volumn 44, Issue 51, 2003, Pages 9155-9159

  Gaeta, Carmine ^a   Martino, Marco ^a   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

Calixarenes; Oxidation; P bromodienone; Transannular spirodienone

Indexed keywords

CALIXARENE; IODIDE; MACROGOL 200; POTASSIUM HYDROXIDE; SODIUM HYDROXIDE;

ARTICLE; OXIDATION; OXYGEN SATURATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; SYNTHESIS;

ARENE;

EID: 0345708157     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.035     Document Type: Article

References (38)

1. For comprehensive reviews on calixarenes see: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713; (b) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998; (c) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens J.; Eds.; Kluwer: Dordrecht, 2001.
2. For comprehensive reviews on calixarenes see: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713; (b) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998; (c) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens J.; Eds.; Kluwer: Dordrecht, 2001.
3. For comprehensive reviews on calixarenes see: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713; (b) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998; (c) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens J.; Eds.; Kluwer: Dordrecht, 2001.
4. Grynszpan F., Aleksiuk O., Biali S.E. Pure Appl. Chem. 68:1996;1249.
5. Aleksiuk O., Grynszpan F., Litwak A.M., Biali S.E. New J. Chem. 20:1996;473 See also Ref. 1c: Biali, S. E.; Chapter 14, pp. 266-279.
6. Litwak A.M., Biali S.E. J. Org. Chem. 57:1992;1943.
7. For a very recent review, see: Biali S.E. Synlett. 2003;1.
8. 5d (a) Aleksiuk, O.; Grynszpan, F.; Biali, S. E. J. Chem. Soc., Chem. Commun. 1993, 11; (b) Van Gelder, J. M.; Aleksiuk, O.; Biali, S. E. J. Org. Chem. 1996, 61, 8419; (c) Aleksiuk, O.; Cohen, S.; Biali, S. E. J. Am. Chem. Soc. 1995, 117, 9645; (d) Van Gelder, J. M.; Brenn, J.; Thondorf, I.; Biali, S. E. J. Org. Chem. 1997, 62, 3511.
9. 5d (a) Aleksiuk, O.; Grynszpan, F.; Biali, S. E. J. Chem. Soc., Chem. Commun. 1993, 11; (b) Van Gelder, J. M.; Aleksiuk, O.; Biali, S. E. J. Org. Chem. 1996, 61, 8419; (c) Aleksiuk, O.; Cohen, S.; Biali, S. E. J. Am. Chem. Soc. 1995, 117, 9645; (d) Van Gelder, J. M.; Brenn, J.; Thondorf, I.; Biali, S. E. J. Org. Chem. 1997, 62, 3511.
10. 5d (a) Aleksiuk, O.; Grynszpan, F.; Biali, S. E. J. Chem. Soc., Chem. Commun. 1993, 11; (b) Van Gelder, J. M.; Aleksiuk, O.; Biali, S. E. J. Org. Chem. 1996, 61, 8419; (c) Aleksiuk, O.; Cohen, S.; Biali, S. E. J. Am. Chem. Soc. 1995, 117, 9645; (d) Van Gelder, J. M.; Brenn, J.; Thondorf, I.; Biali, S. E. J. Org. Chem. 1997, 62, 3511.
11. 5d (a) Aleksiuk, O.; Grynszpan, F.; Biali, S. E. J. Chem. Soc., Chem. Commun. 1993, 11; (b) Van Gelder, J. M.; Aleksiuk, O.; Biali, S. E. J. Org. Chem. 1996, 61, 8419; (c) Aleksiuk, O.; Cohen, S.; Biali, S. E. J. Am. Chem. Soc. 1995, 117, 9645; (d) Van Gelder, J. M.; Brenn, J.; Thondorf, I.; Biali, S. E. J. Org. Chem. 1997, 62, 3511.
12. Agbaria K., Wöhnert J., Biali S.E. J. Org. Chem. 66:2001;7059.
13. Agbaria K., Biali S.E. J. Am. Chem. Soc. 123:2001;12495.
14. 8b see: (a) Grynszpan, F.; Biali, S. E. J. Org. Chem. 1996, 61, 9512; (b) Consoli, G. M. L.; Geraci, C.; Cunsolo, F.; Neri, P. Tetrahedron Lett. 2003, 44, 53.
15. 8b see: (a) Grynszpan, F.; Biali, S. E. J. Org. Chem. 1996, 61, 9512; (b) Consoli, G. M. L.; Geraci, C.; Cunsolo, F.; Neri, P. Tetrahedron Lett. 2003, 44, 53.
16. The procedure has also been extended to spherand-type calixarenes [(a) Agbaria, K.; Aleksiuk, O.; Biali, S. E.; Böhmer, V.; Frings, M.; Thondorf, I. J. Org. Chem. 2001, 66, 2891] and to calix[4]naphthalenes [(b) Georghiou, P. E.; Ashram, M.; Clase, H. J.; Bridson, J. N. J. Org. Chem. 1998, 63, 1819].
17. The procedure has also been extended to spherand-type calixarenes [(a) Agbaria, K.; Aleksiuk, O.; Biali, S. E.; Böhmer, V.; Frings, M.; Thondorf, I. J. Org. Chem. 2001, 66, 2891] and to calix[4]naphthalenes [(b) Georghiou, P. E.; Ashram, M.; Clase, H. J.; Bridson, J. N. J. Org. Chem. 1998, 63, 1819].
18. Wang W.-G., Zhang W.-C., Huang Z.-T. J. Chem. Res. (S). 1998;462.
19. Litwak A.M., Grynszpan F., Aleksiuk O., Cohen S., Biali S.E. J. Org. Chem. 58:1993;393.
20. Gaeta C., Gregoli L., Martino M., Neri P. Tetrahedron Lett. 43:2002;8875.
21. Geraci C., Piattelli M., Chessari G., Neri P. J. Org. Chem. 65:2000;5143. and references cited therein.
22. 2: C, 73.31%; H, 7.98%; Br, 10.36%. Found: C, 73.19%; H, 7.81%; Br, 10.19%.
23. Tee O.S., Iyengar N.R., Paventi M. J. Org. Chem. 48:1983;759.
24. Tee O.S., Iyengar N.R. J. Am. Chem. Soc. 107:1985;455.
25. Rieker A., Berger S. Org. Magn. Reson. 4:1972;857.
26. 2v cis geometry.
27. 2. The presence of a Lewis acidic metal atom was considered very important for the reaction outcome, since no reaction was observed for p-tert-butylcalix[4]arene under identical conditions, see: Radius U., Attner J. Eur. J. Inorg. Chem. 2002;161.
28. 2,3 However, currently the phenoxy radicals route is considered more plausible.
29. Iwamoto K., Araki K., Shinkai S. J. Org. Chem. 56:1991;4955.
30. 4Br: C, 74.53%; H, 8.61%; Br, 9.35%. Found: C, 74.31%; H, 8.76%; Br, 9.20%.
31. Molecular modeling was performed with MacroModel-7.2/Maestro-4.1 program: Mohamadi F., Richards N.G., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. J. Comput. Chem. 11:1990;440.
32. See Ref. 1c: Biali, S. E.; Chapter 14, p. 276.
33. Paquette L.A., Hefferon G.J., Samodral R., Hanzawa Y. J. Org. Chem. 48:1983;1262.
34. 8: C, 81.81%; H, 8.91%. Found: C, 81.58%; H, 9.03%.
35. Tashiro M., Fukata G. Synthesis. 1979;602.
36. Tashiro M., Itoh T., Yoshiya H., Fukata G. Org. Prep. Proced. Int. 16:1984;155.
37. Fukata G., Itoh T., Tashiro M. Heterocycles. 16:1981;549.
38. Fukata G., Itoh T., Tashiro M. Heterocycles. 19:1982;1487.