Oxidations of sulfur rich heterocycles - New S-oxides of the parent 1,2,4-trithiolane and its tetramethyl derivative: Synthesis and structural investigations

Inorganica Chimica Acta

Volumn 357, Issue 6, 2004, Pages 1897-1908

  Petzold, Holm ^a   Bräutigam, Silvio ^a   Görls, Helmar ^a   Weigand, Wolfgang ^a   Uhlemann, Ute ^a   Geßner, Ralph ^b   Kiefer, Wolfgang ^b   Popp, J Ürgen ^a   Majchrzak, Agnieszka ^c   Mloston, Grzegorz ^c  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c UNIVERSITY OF LODZ   (Poland)

Author keywords

1,2,4 Trithiolane S oxides; Ab initio calculations; Crystal structures; Raman spectroscopy; Sulfur heterocycles

Indexed keywords

CALCULATIONS; CRYSTAL STRUCTURE; MIXTURES; RAMAN SPECTROSCOPY; STEREOCHEMISTRY;

AB INITIO CALCULATIONS; M-CHLOROPERBENZOIC ACID (MCPBA); S OXIDES; STRUCTURAL INVESTIGATION; SULFUR HETEROCYCLES; VIBRATIONAL ASSIGNMENT; VIBRATIONAL WAVENUMBERS; X RAY STRUCTURE ANALYSIS;

OXIDATION;

1,2,4 TRITHIOLANE 1 OXIDE; 1,2,4 TRITHIOLANE 1,4 DIOXIDE; 3 CHLOROPERBENZOIC ACID; 3,3,5,5 TETRAMETHYL 1,2,4 TRITHIOLANE; 3,3,5,5 TETRAMETHYL 1,2,4 TRITHIOLANE 1,1,4,4 TETRAOXIDE; 3,3,5,5 TETRAMETHYL 1,2,4 TRITHIOLANE 1,4 DIOXIDE; ANTIBIOTIC AGENT; HETEROCYCLIC COMPOUND; METHYL GROUP; PERACETIC ACID; SULFUR OXIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CIS TRANS ISOMERISM; CORRELATION ANALYSIS; CRYSTAL STRUCTURE; DRUG SYNTHESIS; OXIDATION KINETICS; RAMAN SPECTROMETRY; X RAY ANALYSIS;

EID: 11144358340     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2003.12.004     Document Type: Article

References (29)

1. Moore R.E., Roller P., Au K. Chem. Commun. 1972;325.
2. Ishii A., Nakayama J. Rev. Heteroatom. Chem. 19:1999;1.
3. Wratten S.J., Falkner D.J. J. Org. Chem. 41:1976;2465.
4. Chen C.-C., Chin C.T. J. Agr. Food Chem. 34:1986;830.
5. Chen C.-C., Ho C.-T. J. Chromatogr. 356:1986;455.
6. Wu C.M., Wang Z. Food Sci. Technol. Res. 6:2000;166.
7. Miyazawa M., Osman F. Nat. Prod. Lett. 15:2001;171.
8. Ritzau M., Keller M., Wessels P., Stetter K.O., Zeeck A. Liebigs Ann. Chem. 1993;871.
9. Mloston G., Romanski J., Reisenauer H.P., Maier G. Angew. Chem. 113:2001;401.
10. Angew. Chem. Int. Ed. Engl. 40:2001;393.
11. Fabian J., Senning A. Sulfur Rep. 21:1998;1.
12. Morita K., Kobayashi S. Chem. Pharm. Bull. 15:1967;988.
13. Mloston G., Heimgartner H. Helv. Chim. Acta. 78:1995;1298.
14. Hegab M.I., Abdel-Megeid F.M.E., Gad F.A., Shiba S.A., Søtofte I., Møller J., Senning A. Acta Chem. Scand. 53:1999;133.
15. Steudel R. Chem. Rev. 102:2002;3905. and references cited therein.
16. Bock H., Hirabayashi T., Mohamed S. Chem. Ber. 115:1982;492.
17. G. Mloston, A. Majchrzak, University of Lodz, unpublished results.
18. A. Majchrzak, G. Mloston, E. Ostrycharz, J. Skarzewski, W. Weigand, in: The Sixth International Conference on Heteroatom Chemistry, 22-27 June 2001, Lodz, Poland, Book of Abstracts P-25, p. 153.
19. Oshida H., Ishii A., Nakayama J. Tetrahedron Lett. 43:2002;5033.
20. Asinger F., Thiel M., Lipfert G. Liebigs Ann. Chem. 627:1959;195.
21. Gaussian 98, Revision A.7, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
22. COLLECT, Data Collection Software; Nonius B.V., Netherlands 1998.
23. Otwinowski Z., Minor W. Processing of X-ray diffraction data collected in oscillation mode. Carter C.W., Sweet R.M. Macromolecular Crystallography, Part A. Methods in Enzymology. vol. 276:1997;307 Academic Press.
24. Sheldrick G.M. Acta Crystallogr. A. 46:1990;467.
25. Sheldrick G.M. SHELXL-97 (Release 97-2). 1997;University of Göttingen, Germany.
26. Weigand W., Wünsch R., Robl C., Mloston G., Nöth H., Schmidt M. Z. Naturforsch. B. 55:2000;453.
27. Huisgen R., Mloston G., Polborn K. J. Org. Chem. 61:1996;6570.
28. Braga D., Grepioni F., Desiraju G.R. Chem. Rev. 98:1998;1375.
29. Domagala M., Grabowski S.J., Urbaniak K., Mloston G. J. Phys. Chem. A. 107:2003;2730.