Synthesis and characterization of aliphatic α-dithiones, di(1-adamantyl)- and di-tert-butylethanedithiones

Journal of the American Chemical Society

Volumn 125, Issue 40, 2003, Pages 12114-12115

  Ono, Yutaka ^a   Sugihara, Yoshiaki ^a   Ishii, Akihiko ^a   Nakayama, Juzo ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC COMPOUND; DI TERT BUTYL ETHANEDITHIONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; CRYSTALLIZATION; DESULFURIZATION; ELECTRON TRANSPORT; ISOMERISM; MASS SPECTROMETRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0141992318     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0371496     Document Type: Article

References (32)

1. (a) Küsters, W.; de Mayo, P. J. Am. Chem. Soc. 1973, 95, 2383-2384.
2. (b) Küsters. W.; de Mayo, P. J. Am. Chem. Soc. 1974, 96, 3502-3511.
3. 2. Dithiooxalamides and related compounds, stabilized by push-pull effects, are known; see references cited in ref 7b.
4. For the latest review, see: Nakayama, J.; Ishii, A. Adv. Heterocycl. Chem. 2000, 77, 221-284.
5. 3
6. (a) Krespan, C. G.; McKusick, B. C.; Cairns, T. L. J. Am. Chem. Soc. 1960, 82, 1515-1516.
7. (b) Krespan, C. G. J, Am. Chem. Soc. 1961, 83, 3434-3437.
8. (c) Krespan, C. G.; McKusick. B. C. J. Am. Chem. Soc. 1961. 83, 3438-3440.
9. Shimizu. T.; Murakami. H.; Kobayashi, Y.; Iwata, K.; Kamigata, N. J. Org. Chem. 1998, 63, 8192-8199.
10. (a) Nakayama, J.; Choi, K. S.; Akiyama, I.; Hoshino, M. Tetrahedron Lett. 1993, 34, 115-118.
11. (b) Choi, K. S.; Akiyama, I.; Hoshino, M.; Nakayama. J. Bull. Chem. Soc. Jpn. 1993, 66. 623-629.
12. (a) Boar, R. B.; Hawkins, D. W.; McGhie. J. F.; Misra, S. C.; Barton, D. H. R.; Ladd. M. F. C.; Povery, D. C. J. Chem. Soc., Chem. Commun. 1975, 756.
13. (b) Krebs, A.; Colberg, H.; Höpfner, U.; Kimling, H.; Odenthal. J. Heterocycles 1979, 12, 1153-1156.
14. (c) Köpke, B.; Voss, J. J. Chem. Res.. Synop. 1982, 314-315.
15. (a) Nakayama, J.; Takahashi, K.; Watanabe, T.; Sugihara, Y.; Ishii, A. Tetrahedron Lett. 2000, 41, 8349-8352.
16. (b) Nakayama. J.; Takahashi, K.; Sugihara, Y.; Ishii, A. Tetrahedron Lett. 2001, 42, 4017-4019.
17. (c) Nakayama, J.; Takahashi, K.; Ono, Y.; Morita, M.; Sugihara, Y.; Ishii, A. Heteroat. Chem. 2002, 13, 424-429.
18. Kutney, G. W.; Turnbull, K. Chem. Rev. 1982, 82. 333-357.
19. +), 358.1789; found, 358.1780.
20. In the El mode, the fragmentation pattern of 8 resembles that of 6 closely because of probable isomerization of 8 to 6 prior to the ionization.
21. (a) The calculations have been performed by using the Gaussian 98 (revision A.7) program on personal computers running RedHat Linux 7.2.
22. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N. ; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham. M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
23. Vibration modes were visualized by Gauss View 2.1 program. Gaussian, Inc.: Pittsburgh, PA, 2000.
24. max 518 nm.
25. Nakayama. J.: Masui, N.; Sugihara, Y.; Ishii, A. Bull. Chem. Soc. Jpn. 1998, 71, 1181-1186 and references therein.
26. Gasper, P. P.; Harrison, J. F.; Herold, B. J. In Carbene Chemistry, 2nd ed.; Kirmse, W., Ed.; Academic Press: New York and London, 1971; Chapter 9, pp 375-376.
27. Doorakian, G. A.; Freedman, H. H. J. Am. Chem. Soc. 1968, 90, 3582-3584.
28. 1b Such conjugation is not expected for the aliphatic dithione 8, thus conversion of 8 to 6 giving a larger ΔS≠ value than that of 2 to 3.
29. Yokomori, Y.; Nakayama, J. 1994, unpublished results.
30. Donahue, J. P.; Holm, R. H. Acta Crystallogr. 1998, C54, 1175-1178.
31. 3
32. Nakayama, J.; Mizumura, A.; Yokomori, Y.; Krebs, A.; Shütz, K. Tetrahedron Lett. 1995, 36, 8583-8586.