Stereoselective oxidation of thiacalix[4]arenes with the NaNO 3/CF3COOH system

Tetrahedron Letters

Volumn 44, Issue 39, 2003, Pages 7333-7336

  Lhoták, Pavel ^a   Morávek, Jiří ^a   Šmejkal, Tomáš ^a   Stibor, Ivan ^a   Sýkora, Jan ^b  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b INSTITUTE OF CHEMICAL PROCESS FUNDAMENTALS   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; BRIDGED COMPOUND; CALIXARENE; CARBOXYL GROUP; OXIDIZING AGENT; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SODIUM NITRATE; SULFOXIDE; SULFUR DERIVATIVE;

ARTICLE; ATOMIC PARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; X RAY DIFFRACTION;

ARENE;

EID: 0041880515     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01868-9     Document Type: Article

References (25)

1. For books on calixarenes, see: (a) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; (b) Mandolini, L.; Ungaro, R. Calixarenes in Action; Imperial College Press: London, 2000; (c) Gutsche, C. D. Calixarenes Revisited: Monographs in Supramolecular Chemistry Vol. 6.; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998; (d) Calixarenes 50th Aniversary: Commemorative Issue; Vicens, J.; Asfari, Z.; Harrowfield, J. M., Eds.; Kluwer Academic Publishers: Dordrecht, 1994; (e) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991.
2. For books on calixarenes, see: (a) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; (b) Mandolini, L.; Ungaro, R. Calixarenes in Action; Imperial College Press: London, 2000; (c) Gutsche, C. D. Calixarenes Revisited: Monographs in Supramolecular Chemistry Vol. 6.; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998; (d) Calixarenes 50th Aniversary: Commemorative Issue; Vicens, J.; Asfari, Z.; Harrowfield, J. M., Eds.; Kluwer Academic Publishers: Dordrecht, 1994; (e) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991.
3. For books on calixarenes, see: (a) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; (b) Mandolini, L.; Ungaro, R. Calixarenes in Action; Imperial College Press: London, 2000; (c) Gutsche, C. D. Calixarenes Revisited: Monographs in Supramolecular Chemistry Vol. 6.; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998; (d) Calixarenes 50th Aniversary: Commemorative Issue; Vicens, J.; Asfari, Z.; Harrowfield, J. M., Eds.; Kluwer Academic Publishers: Dordrecht, 1994; (e) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991.
4. For books on calixarenes, see: (a) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; (b) Mandolini, L.; Ungaro, R. Calixarenes in Action; Imperial College Press: London, 2000; (c) Gutsche, C. D. Calixarenes Revisited: Monographs in Supramolecular Chemistry Vol. 6.; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998; (d) Calixarenes 50th Aniversary: Commemorative Issue; Vicens, J.; Asfari, Z.; Harrowfield, J. M., Eds.; Kluwer Academic Publishers: Dordrecht, 1994; (e) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991.
5. For books on calixarenes, see: (a) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; (b) Mandolini, L.; Ungaro, R. Calixarenes in Action; Imperial College Press: London, 2000; (c) Gutsche, C. D. Calixarenes Revisited: Monographs in Supramolecular Chemistry Vol. 6.; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998; (d) Calixarenes 50th Aniversary: Commemorative Issue; Vicens, J.; Asfari, Z.; Harrowfield, J. M., Eds.; Kluwer Academic Publishers: Dordrecht, 1994; (e) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991.
6. Kumagai H., Hasegawa M., Miyanari S., Sugawa Y., Sato Y., Hori T., Ueda S., Kamiyama H., Miyano S. Tetrahedron Lett. 38:1997;3971-3972.
7. Iki N., Kabuto C., Fukushima T., Kumagai H., Takeya H., Miyanari S., Miyashi T., Miyano S. Tetrahedron. 56:2000;1437-1443.
8. Lhoták P., Dudic M., Stibor I., Petrickova H., Sykora J., Hodacova J. J. Chem. Soc., Chem. Commun. 2001;731.
9. Katagiri H., Iki N., Hattori T., Kabuto C., Miyano S. J. Am. Chem. Soc. 123:2001;779.
10. Iki H., Kumagai H., Morohashi N., Ejima K., Hasegawa M., Miyanari S., Miyano S. Tetrahedron Lett. 39:1998;7559.
11. Morohashi N., Iki N., Sugawara A., Miyano S. Tetrahedron. 57:2001;5557.
12. Mislin G., Graf E., Hosseini M.W., De Cian A., Fischer J. Tetrahedron Lett. 40:1999;1129.
13. Morohashi N., Iki N., Kabuto C., Miyano S. Tetrahedron Lett. 41:2000;2933.
14. Lhoták P., Morávek J., Stibor I. Tetrahedron Lett. 43:2002;3665.
15. Lhoták P., Svoboda J., Stibor I., Sykora J. Tetrahedron Lett. 43:2002;7413.
16. Lhoták P. Tetrahedron. 57:2001;4775.
17. 3COOH system in 60% yield. See: Arduini A., Mirone L., Paganuzzi D., Pinalli A., Pochini A., Secchi A., Ungaro R. Tetrahedron. 52:1996;6011.
18. 3. Yield 74%.
19. 3/HF system was used for the oxidation of 1,4-dithiino[2,3-c:6,5-c]diisothiazole to the corresponding disulfoxide. See: Vladuchick S.A., Fukunaga T., Simmons H.E., Webster O.W. J. Org. Chem. 45:1980;5122.
20. 3 as the oxidising agent. Yield 87%.
21. Sato K., Hyodo M., Aoki M., Zheng X.Q., Noyori R. Tetrahedron. 57:2001;2469-2476.
22. max=67.9°). Ethyl acetate solvent molecule was localised from the difference Fourier map. Hydrogen atoms were located from expected geometry and were not refined. Ψ-scan was used for absorption correction. Crystallographic data were deposited in CSD under CCDC registration number 196007.
23. Altomare, A.; Cascarano, G.; Giacovazzo G.; Guagliardi A.; Burla M. C.; Polidori, G.; Camalli, M. SIR-92: A Program for Automatic Solution of Crystal Structures by Direct Methods J. Appl. Crystallogr. 1994, 27, 435.
24. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W.; Cooper, R. I. CRYSTALS, Issue 11, Chemical Crystallography Laboratory, Oxford, UK, 2001.
25. Morohashi N., Katagiri H., Iki N., Yamane Y., Kabuto C., Hattori T., Miyano S. J. Org. Chem. 68:2003;2324.