Synthesis of sulfur-rich 1,2-and 1,3-dithiolo disulfides and thiodesaurines from diisopropyl sulfide

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4376-4380

  Rees, Charles W ^a   Rakitin, Oleg A ^b   Marcos, Carlos F ^c   Torroba, Tomás ^d  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^c UNIVERSITY OF EXTREMADURA   (Spain)

^d UNIVERSITY OF BURGOS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; 4 ISOPROPYLTHIO 5 ISOPROPYLDITHIO 1,2 DIOTHIOLE 3 THIONE; 4,5 DI(ISOPROPYLTHIO) 1,2 DITHIOLE 3 THIONE; 5,5' DITHIO BIS(4 ISOPROPYLTHIO 1,2 DITHIOL 3 THIONE); BENZENE; CHLOROBENZENE; DICHLOROMETHANE; DISULFIDE; PHOSPHINE DERIVATIVE; SULFIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS; ULTRAVIOLET IRRADIATION;

EID: 0033546097     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9825005     Document Type: Article

References (54)

1. (a) Garín, J. Adv. Heterocycl. Chem. 1995, 62, 249.
2. (b) Misaki, Y.; Fujiwara, H.; Yamabe, T. J. Org. Chem. 1996, 61, 3650.
3. (c) Otsubo, T.; Aso, Y.; Takimiya, K. Adv. Mater. 1996, 8, 203.
4. (d) Horiuchi, S.; Yamochi, H.; Saito, G.; Sakaguchi, K.; Kusunoki, M. J. Am. Chem. Soc. 1996, 118, 8604.
5. (e) Roncali, J. J. Mater. Chem. 1997, 7, 2307.
6. (a) Tsivgoulis, G. M.; Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1119.
7. (b) Gilat, S. L.; Kawai, S. H.; Lehn, J.-M. Chem. Eur. J. 1995, 1, 275.
8. (c) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem. Eur. J. 1995, 1, 285.
9. (d) Tsivgoulis, G. M.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1399.
10. (e) Tsivgoulis, G. M.; Lehn, J.-M. Adv. Mater. 1997, 9, 39.
11. (a) Kensler, T. W.; Groopman, J. D.; Roebuck, B. D.; Curphey, T. J. ACS Symp. Ser. 1994, 546, 154.
12. (b) Maxuitenko, Y. Y.; Curphey, T. J.; Kensler, T. W.; Roebuck, B. D. Fundam. Appl. Toxicol. 1996, 32, 250.
13. (c) Drukarch, B.; Schepens, E.; Stoof, J. C.; Langeveld, C. H. Eur. J. Pharmacol. 1997, 329, 259.
14. (d) Kim, W.; Gates, K. S. Chem. Res. Toxicol. 1997, 10, 296.
15. (a) Fleury, M. B.; Largeron, M.; Martens, T. Biochem. Pharmacol. 1991, 41, 361.
16. (b) Ahmed, S. A.; Gad, M. Z. Arzn.-Forsch./Drug Res. 1995, 45-2, 1324.
17. (a) Kensler, T. W.; Helzlsouer, K. J. J. Cell Biochem. 1995, 101.
18. (b) O'Dwyer, P. J.; Johnson, S. W.; Khater, C.; Krueger, A.; Matsumoto, Y.; Hamilton, T. C.; Yao, K. S. Cancer Res. 1997, 57, 1050.
19. (c) Langouet, S.; Maheo, K.; Berthou, F.; Morel, F.; Gossman, D. L.; Glaise, D.; Coles, B.; Ketterer, B.; Guillouzo, A. Carcinogenesis 1997, 18, 1343.
20. (a) Prochaska, H. J.; Chavan, S. J.; Baron, P.; Polsky, B. J. Cell. Biochem. 1995, 117.
21. (b) Prochaska, H. J.; Bornmann, W. G.; Baron, P.; Polsky, B. Mol. Pharmacol. 1995, 48, 15.
22. (c) Prochaska, H. J.; Fernandes, C. L.; Pantoja, R. M.; Chavan, S. J. Biochem. Biophys. Res. Commun. 1996, 221, 548.
23. (a) Plater, M. J.; Rees, C. W.; Roe, D. G.; Torroba, T. J. Chem. See., Chem. Commun. 1993, 293; J. Chem. Soc., Perkin Trans. 1 1993, 769.
24. (a) Plater, M. J.; Rees, C. W.; Roe, D. G.; Torroba, T. J. Chem. See., Chem. Commun. 1993, 293; J. Chem. Soc., Perkin Trans. 1 1993, 769.
25. (b) Polo, C.; Rakitin, O. A.; Ramos, V.; Rees, C. W.; Torroba, T. Tetrahedron 1998, 54, 223.
26. (a) Rakitin, O. A.; Rees, C. W.; Torroba, T. J. Chem. Soc., Chem. Commun. 1996, 427.
27. (b) Rakitin, O. A.; Rees, C. W.; Williams, D. J.; Torroba, T. J. Org. Chem. 1996, 61, 9178.
28. Barberá, J.; Rakitin, O. A.; Ros, M. B.; Torroba, T. Angew. Chem., Int. Ed. Engl. 1998, 37, 296.
29. Marcos, C. F.; Polo, C.; Rakitin, O. A.; Rees, C. W.; Torroba, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 281.
30. Marcos, C. F.; Polo, C.; Rakitin, O. A.; Rees, C. W.; Torroba, T. J. Chem. Soc., Chem. Commun. 1997, 879.
31. Marcos, C. F.; Rakitin, O. A.; Rees, C. W.; Souvorova, L. L.; Torroba, T.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1998, 453.
32. Rees, C. W.; White, A. J. P.; Williams, D. J.; Rakitin, O. A.; Marcos, C. F.; Polo, C.; Torroba, T. J. Org. Chem. 1998, 63, 2189.
33. Boisson, C.; Berthet, J. C.; Lance, M.; Nierlich, M.; Ephritikhine, M. J. Chem. Soc., Chem. Commun. 1996, 2129.
34. (a) Minkwitz, R.; Kornath, A.; Krause, R.; Preut, H. Z. Naturforsch. 1990, 45b, 1637; Z. Anorg. Allg. Chem. 1994, 620, 632.
35. (a) Minkwitz, R.; Kornath, A.; Krause, R.; Preut, H. Z. Naturforsch. 1990, 45b, 1637; Z. Anorg. Allg. Chem. 1994, 620, 632.
36. (b) R. Minkwitz, U. Lohmann, Z. Anorg. Allg. Chem 1996, 622, 557.
37. (a) Moore, C. G.; Porter, M. J. Chem. Soc. 1958, 2890.
38. (b) Pietra, F.; Vitali D. J. Chem. Soc. B 1970, 623.
39. (a) Pedersen, C. Th. Adv. Heterocycl. Chem. 1982, 31, 63.
40. (b) McKinnon, D. M. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, Chapter 4.31. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996; Vol. 3, Chapter 3.11.
41. (b) McKinnon, D. M. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, Chapter 4.31. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996; Vol. 3, Chapter 3.11.
42. For some recent examples of 1:1 aducts, see: (a) Leriche, P.; Belyasmine, A.; Sallé, M.; Frère, P.; Gorgues, A.; Riou, A.; Jubault, M.; Orduna, J.; Garín, J. Tetrahedron Lett. 1996, 37, 8861. (b) Fanghänel, E.; Palmer, T.; Kersten, J.; Ludwigs, R.; Peters, K.; von Schnering, H. G. Synthesis 1994, 1067. (b) Doxsee, D. D.; Galloway, C. P.; Rauchfuss, T. B.; Wilson, S. R.; Yang, X. Inorg. Chem. 1993, 32, 5467.
43. For some recent examples of 1:1 aducts, see: (a) Leriche, P.; Belyasmine, A.; Sallé, M.; Frère, P.; Gorgues, A.; Riou, A.; Jubault, M.; Orduna, J.; Garín, J. Tetrahedron Lett. 1996, 37, 8861. (b) Fanghänel, E.; Palmer, T.; Kersten, J.; Ludwigs, R.; Peters, K.; von Schnering, H. G. Synthesis 1994, 1067. (b) Doxsee, D. D.; Galloway, C. P.; Rauchfuss, T. B.; Wilson, S. R.; Yang, X. Inorg. Chem. 1993, 32, 5467.
44. For some recent examples of 1:1 aducts, see: (a) Leriche, P.; Belyasmine, A.; Sallé, M.; Frère, P.; Gorgues, A.; Riou, A.; Jubault, M.; Orduna, J.; Garín, J. Tetrahedron Lett. 1996, 37, 8861. (b) Fanghänel, E.; Palmer, T.; Kersten, J.; Ludwigs, R.; Peters, K.; von Schnering, H. G. Synthesis 1994, 1067. (b) Doxsee, D. D.; Galloway, C. P.; Rauchfuss, T. B.; Wilson, S. R.; Yang, X. Inorg. Chem. 1993, 32, 5467.
45. (a) Demarcq, M. C. J. Chem. Res., Synop. 1993, 450.
46. (b) Bohle, M.; Liebscher, J. Adv. Heterocycl. Chem. 1996, 65, 39.
47. (a) Behringer, H.; Meinetsberger, E. Liebigs Ann. Chem. 1981, 1729.
48. (b) Amzil, J.; Catel, J. M.; le Coustumer, G.; Mollier, Y.; Sauve, J. P. Bull. Soc. Chim. Fr. 1988, 101.
49. (c) Rudershausen, S.; Holdt, H.-J.; Reinke, H.; Drexler, H.-J.; Michalik, M.; Teller, J. J. Chem. Soc., Chem. Commun. 1998, 1653.
50. Dipolar moments for 14 and 15 were calculated with Hyper-Chem 5.0 on PM3 optimized geometries.
51. 5,5′-Dithiobis(4-chloro-1,2-dithiol-3-one) has been reported: Bader, J. Helv. Chim. Acta 1968, 51, 1409.
52. (a) Kang, H.; Fenical, W. Tetrahedron Lett. 1996, 37, 2369.
53. (b) Radchenko, O. S.; Novikov, V. L.; Willis, R. H.; Murphy, P. T.; Elyakov, G. B. Tetrahedron Lett. 1997, 38, 3581.
54. Aimar, M. L.; Rossi, R. H. Tetrahedron Lett. 1996, 37, 2137.