Significant intramolecular sulfur-sulfur interactions in cis- and trans-2,3-dimethyl-5,6-dithiabicyclo-[2.1.1]hexane

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 525-528

  Block, Eric ^a   Glass, Richard S ^b   DeOrazio, Russell ^a   Lichtenberger, Dennis L ^b   Pollard, John R ^b   Russell, Erin E ^b   Schroeder, T Benjamin ^b   Thiruvazhi, Mohan ^a   Toscano, Paul J ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002986646     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6136     Document Type: Article

References (38)

1. (a) Jørgensen, F.S.; Snyder, J.P. J. Org. Chem. 1980, 45, 1015.
2. (b) Rindorf, G.; Jørgensen, F.S.; Snyder, J.P. J. Org. Chem. 1980, 45, 5343.
3. (a) Jørgensen, F.S.; McCabe, P.H. Tetrahedron Lett. 1983, 24, 319.
4. (b) Brown, R.S.; Jørgensen, F.S. in "Electron Spectroscopy: Theory, Techniques and Applications," Vol. 5, Brandle, C.R.; Baker, A.D., Eds., Academic: London, 1984, pp 1-122.
5. (a) Glass, R.S.; Hojjatie, M.; Petsom, A.; Wilson, G.S.; Göbl, M.; Mahling, S.; Asmus, K.-D. Phosphorus and Sulfur 1985, 23, 143.
6. (b) Glass, R.S.; Andruski, S.W.; Broeker, J.L. Rev. Heteroatom Chem. 1988, 1, 31.
7. (c) Glass, R.S.; Andruski, S.W.; Broeker, J.L.; Firouzabadi, H.; Steffen, L.K.; Wilson, G.S. J. Am. Chem. Soc. 1989, 111, 4036.
8. Block, E.; Corey, E.R.; Penn, R.E.; Renken, T.L.; Sherwin, P.F.; Bock, H.; Hirabayshi, T.; Mohmand, S.; Solouki, B. J. Am. Chem. Soc. 1982, 104, 3119.
9. Block, E.; Thiruvazhi, M.; Toscano, P.J.; Bayer, T.; Grisoni, S.; Zhao, S.-H. J. Am. Chem.Soc. 1996, 118, 2790.
10. 6b
11. (b) Block, E.; DeOrazio, R.; Thiruvazhi, M. J. Org. Chem. 1994, 59, 2273.
12. (a) Ishii, A.; Nakayama, J.; Ding, M.; Kotaka, N.; Hoshino, M. J. Org. Chem. 1990, 55, 2421.
13. (b) Ishii, A.; Ding, M.; Maeda, K.; Nakayama, J.; Hoshino, M. Bull. Chem. Soc. Jpn. 1992, 65, 3343.
14. (a) Pitchen, P.; Deshmukh, M.; Dunach, E.; Kagan, H.B. J. Am. Chem. Soc. 1984, 106, 8188.
15. (b) Nemecek, E.; Dunach, E.; Kagan, H.B. New J. Chem. 1986, 10, 761.
16. (c) While 2a and 3a are racemates, for convenience we have arbitrarily chosen to display these structures in one enantiomeric form.
17. (a) Nicolaou, K.C.; DeFrees, S.A.; Hwang, C.-K.; Stylianides, N.; Carroll, P.J.; Snyder, J.P. J. Am. Chem. Soc. 1990, 112, 3029.
18. (b) Ishii, A.; Akazawa, T.; Maruta, T.; Nakayama, J.; Hoshino, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 777.
19. (c) Ishii, A.; Jin, Y.-N.; Nagaya, H.; Hoshino, M.; Nakayama, J. Tetrahedron Lett. 1995, 36, 1867.
20. Krebs, B.; Beyer, H. Z. Anorg. Allg. Chem. 1969, 365, 199.
21. Mikolajczyk, M.; Kielbasinski, P.; Barlow, J.H.; Russell, D.R. J. Org. Chem. 1977, 42, 2345.
22. (a) For cis isomer 2b: 8.11 eV (FWHM = 0.36 eV), 9.03 eV (FWHM = 0.32 eV); trans isomer 2a: 8.11 eV (FWHM = 0.36 eV), 9.03 eV (FWHM = 0.32 eV).
23. 9a
24. Hoffman, R. Acc. Chem. Res. 1971, 4, 1.
25. B.R. Coleman, Ph.D. Dissertation, The University of Arizona, 1982.
26. Coleman, B.R.; Glass, R.S.; Setzer, W.N.; Prabhu, U.D.G.; Wilson, G.S. Adv. Chem. Ser. 1982, 201, 417.
27. DA, the mean separation of donor and acceptor, due to differences in steric hindrance.
28. Asmus, K.D. Acc. Chem. Res. 1979, 12, 436.
29. 18d We estimate that the strain energy for 5,6-dithiabicyclo-[2.1.1]hexane is ca. 26 kcal/mol.
30. (b) Allinger, N.L. unpublished results personally communicated.
31. (c) Tabushi, I.; Tamaru, Y.; Yoshida, Z. Tetrahedron Lett. 1970, 2931.
32. (d) Allinger, N.L.; Hickey, M.J. J. Am. Chem. Soc. 1975, 97, 5167.
33. (a) Calabro, D.C.; Hubbard, J.L.; Blevins 11, C.H.; Campbell, A.C.; Lichtenberger D.L. J. Am. Chem. Soc. 1981, 103, 6739.
34. (b) Lichtenberger, D.L.; Kellogg, G.E.; Kristofzski, J.G.; Page, D.; Turner, S.; Klinger, G.; Lorenzen, J. Rev. Sci. Instrum. 1986, 57, 2366.
35. (c) Hubbard, J.L. Diss. Abst. Intl. 1983, 43, 2203.
36. SPARTAN 4.0 User's Guide, Wavefunction Inc., Irvine CA, 1996.
37. Hehre, W.J.; Radom, L.; Schleyer, P.v.R.; Pople, J.A. Ab initio Molecular Orbital Theory, Wiley: NY, 1986.
38. The authors have deposited atomic coordinates for compound 2c with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.