Stereocontrolled oxidation of a thiacalix[4]arene to the sulfinyl counterpart of a defined S=O configuration

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2933-2937

  Morohashi, Naoya ^a   Iki, Nobuhiko ^a   Kabuto, Chizuko ^a   Miyano, Sotaro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Calixarenes; Oxidation; Sulfinyl compounds; X ray crystallography

Indexed keywords

CALIXARENE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CONFORMATION; OXIDATION; STEREOCHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

EID: 0034655490     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00313-0     Document Type: Article

References (12)

1. Kumagai, H.; Hasegawa, M.; Miyanari, S.; Sugawa, Y.; Sato, Y.; Hori, T.; Ueda, S.; Kamiyama, H.; Miyano, S. Tetrahedron Lett. 1997, 38, 3971-3972.
2. Iki, N.; Morohashi, N.; Narumi, F.; Fujimoto, T.; Suzuki, T.; Miyano, S. Tetrahedron Lett. 1999, 40, 7337-7341, and Ref. 2-7 cited therein.
3. Iki, N.; Morohashi, N.; Narumi, F.; Miyano, S. Bull. Chem. Soc. Jpn. 1998, 71, 1597-1603.
4. Iki, N.; Morohashi, N.; Kabuto, C.; Miyano, S. Chem. Lett. 1999, 219-220.
5. Iki, N.; Kumagai, H.; Morohashi, N.; Ejima, K.; Hasegawa, M.; Miyanari, S.; Miyano, S. Tetrahedron Lett. 1998, 39, 7559-7562.
6. Mislin, G.; Graf, E.; Hosseini, M. W.; Cian, A. D.; Fischer, J. Tetrahedron Lett. 1999, 40, 1129-1132.
7. 4: C, 75.51; H, 6.71; S, 11.86. Found: C, 75.26; H, 6.70; S, 12.06.
8. 4: C, 71.29; H, 6.34; S, 11.20. Found: C, 71.50; H, 6.35; S, 11.26.
9. O)), GOF=1.55. Further details of X-ray analysis are available on request from the Director of the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
10. 4: C, 61.19; H, 6.16; S, 16.34. Found: C, 60.98; H, 6.11; S, 16.09. Although it is well known that sulfoxides are highly susceptible to isomerization under strongly acidic conditions, treatment of 2(ttt) with trifluoroacetic acid under the above conditions did not show any indication of the conformational change of 2(ttt).
11. Akdas, H.; Bringel, L.; Graf, E.; Hosseini, M. W.; Mislin, G.; Pansanel, J.; Cian, A. D.; Fischer, J. Tetrahedron Lett. 1998, 39, 2311-2314.
12. Iki, N.; Kabuto, C.; Fukushima, T.; Kumagai, H.; Takeya, H.; Miyanari, S.; Miyashi, T.; Miyano, S. Tetrahedron 2000, 56, 1437-1443.