Formation, structure, and thionation of 1,2,4,5-tetrathianes [cis- and trans-3,6-bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)1,2,4,5-tetrathianes]

Bulletin of the Chemical Society of Japan

Volumn 73, Issue 3, 2000, Pages 729-737

  Ishii, Akihiko ^a   Omata, Takenori ^a   Umezawa, Kazuyo ^a   Nakayama, Juzo ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BICYCLO COMPOUND; CYCLOALKANE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; SYNTHESIS; TEMPERATURE DEPENDENCE; X RAY CRYSTALLOGRAPHY;

EID: 0034027468     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.73.729     Document Type: Article

References (39)

1. For a review, see: M. J. Cook, in "Comprehensive Heterocyclic Chemistry," ed by A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford (1984), Vol. 3, Chap. 2.26, pp. 943-994.
2. R. Susilo, R. Gmelin, K. Roth, and H. Bauer, Z. Naturforsch., B, 37b, 234 (1982).
3. a) C. H. Bushweller, J. Am. Chem. Soc., 89, 5978 (1967).
4. b) C. H. Bushweller, J. Am. Chem. Soc., 91, 6019 (1969).
5. c) C. H. Bushweller, J. Golini, G. U. Rao, and J. W. O'Neil, J. Chem. Soc., Chem. Commun., 1970, 51.
6. d) C. H. Bushweller, J. Golini, G. U. Rao, and J. W. O'Neil, J. Am. Chem. Soc., 92, 3055 (1970).
7. a) C. H. Bushweller, Tetrahedron Lett., 1968, 2785.
8. b) C. H. Bushweller, G. U. Rao, and F. H. Bissett, J. Am. Chem. Soc., 93, 3058 (1971).
9. c) C. H. Bushweller, G. Bhat, L. J. Letendre, J. A. Brunelle, H. S. Bilofsky, H. Ruben, D. H. Templeton, and A. Zalkin, J. Am. Chem. Soc., 97, 65 (1975).
10. R. Huisgen and J. Rapp, Heterocycles, 45, 507 (1997).
11. G. W. Kutney and I. W. J. Still, Can. J. Chem., 58, 1233 (1980).
12. A. Elsäßer and W. Sundermeyer, Chem. Ber., 118, 4553 (1985).
13. Y. Takikawa, T. Makabe, N. Hirose, T. Hiratsuka, R. Takoh, and K. Shimada, Chem. Lett., 1988, 1517.
14. F. A. G. El-Essawy, S. M. Yassin, I. A. El-Sakka, A. F. Khattab, I. Søtofte, J. Ø. Madsen, and A. Senning, J. Org. Chem., 63, 9840 (1998).
15. a) A. Ishii, T. Akazawa, M.-X. Ding, T. Honjo, T. Maruta, S. Nakamura, H. Nagaya, M. Ogura, K. Teramoto, M. Shiro, M. Hoshino, and J. Nakayama, Bull. Chem. Soc. Jpn., 70, 509 (1997).
16. b) A. Ishii, K. Umezawa, and J. Nakayama, Tetrahedron Lett., 38, 1431 (1997).
17. c) A. Ishii, T. Maruta, K. Teramoto, and J. Nakayama, Sulfur Lett., 18, 237 (1995).
18. d) A. Ishii, Y.-N. Jin, H. Nagaya, M. Hoshino, and J. Nakayama, Tetrahedron Lett., 36, 1867 (1995).
19. e) A. Ishii, Y.-N. Jin, M. Hoshino, and J. Nakayama, Heteroatom Chem., 6, 161 (1995).
20. f) A. Ishii, T. Akazawa, T. Maruta, J. Nakayama, M. Hoshino, and M. Shiro, Angew. Chem., Int. Ed. Engl., 33, 777 (1994).
21. g) A. Ishii, T. Akazawa, M.-X. Ding, T. Honjo, J. Nakayama, M. Hoshino, and M. Shiro, J. Am. Chem. Soc., 115, 4914 (1993).
22. h) A. Ishii, M.-X. Ding, K. Maeda, J. Nakayama, and M. Hoshino, Bull. Chem. Soc. Jpn., 65, 3343 (1992).
23. i) A. Ishii, J. Nakayama, M.-X. Ding, N. Kotaka, and M. Hoshino, J. Org. Chem., 55, 2421 (1990).
24. B. S. Pedersen, S. Scheibye, N. H. Nilsson, and S.-O. Lawesson, Bull. Soc. Chim. Belg., 87, 223 (1978).
25. A. Ishii, T. Nakaniwa, K. Umezawa, and J. Nakayama, Tetrahedron, 55, 10341 (1999).
26. A. Ishii, M.-X. Ding, J. Nakayama, and M. Hoshino, J. Chem. Soc., Chem. Commun., 1992, 7.
27. J. L. Kice and J. P. Cleveland, J. Am. Chem. Soc., 95, 104 (1973).
28. R. Huisgen and J. Rapp, J. Am. Chem. Soc., 109, 902 (1987); R. Huisgen and J. Rapp, Tetrahedron, 53, 939 (1997).
29. R. Huisgen and J. Rapp, J. Am. Chem. Soc., 109, 902 (1987); R. Huisgen and J. Rapp, Tetrahedron, 53, 939 (1997).
30. K. L. McCormack, P. R. Mallinson, B. C. Webster, and D. S. Yufit, J. Chem. Soc., Faraday Trans., 92, 1709 (1996).
31. J. D. Korp, I. Bernal, S. F. Watkins, and F. R. Fronczek, Tetrahedron Lett., 22, 4767 (1981).
32. N. L. Allinger, M. J. Mickey, and J. Kao, J. Am. Chem. Soc., 98, 2741 (1976).
33. PM3 calculations were performed with WinMOPAC ver. 1.0 (Fujitsu Ltd., 1997) based on MOPAC93 developed by J. J. P. Stewart. The calculations were done with key words of FORCE, THERMO, ROT, and PRECISE. The ΔG° values were obtained from values of the heat of formation and the entropy at respective temperatures.
34. H. Shanan-Atidi and K. H. Bar-Eli, J. Phys. Chem., 74, 961 (1970).
35. M. Oki, "Applications of Dynamic NMR Spectroscopy to Organic Chemistry," Vol. 4 of a series of "Methods in Stereochemical Analysis," ed by A. P. Marchand, VCH Publishers, Inc., Deerfield Beach, Florida (1985).
36. D. D. MacNicol and A. Murphy, Tetrahedron Lett., 22, 1131 (1981).
37. C. H. Bushweller, G. U. Rao, W. G. Anderson, and P. E. Stevenson, J. Am. Chem. Soc., 94, 4743 (1972).
38. S. Scheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 38, 993 (1982).
39. A. Altomare, G. Cascarano, C. Giacovazzo, and A. Guagliardi, J. Appl. Crystallogr., 26, 343 (1993).