Transannular Te-S interaction in a new tellurium heterocycle, 5H,7H-dibenzo[b,g][1,5]tellurathiocin

Organometallics

Volumn 15, Issue 7, 1996, Pages 1913-1919

  Takaguchi, Yutaka ^a   Fujihara, Hisashi ^a,b   Furukawa, Naomichi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000815798     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950831r     Document Type: Article

References (18)

1. Alder, R. W. Tetrahedron 1990, 46, 683.
2. (a) Musker, W. K.; Wolford, T. L.; Roush, P. B. J. Am. Chem. Soc. 1978, 100, 6416.
3. (b) Musker, W. K.; Hirschon, A. S.; Doi, J. T. J. Am. Chem. Soc. 1978, 100, 7754.
4. (a) Fujihara, H.; Chiu, J.-J.; Furukawa, N. J. Am. Chem. Soc. 1988, 110, 1280.
5. (b) Fujihara, H.; Furukawa, N. J. Mol. Struct (Theochem) 1989, 186, 261 and references cited therein.
6. Fujihara, H.; Takaguchi, Y.; Chiu, J.-J.; Furukawa, N. Chem. Lett. 1992, 151.
7. Hayes, R. A.; Martin, J. C. Sulfurane Chemistry. In Organic Sulfur Chemistry, Theoretical and Experimental Advances; Bernardi, F., Csizmadia, I. G., Mangini, A., Eds.; Elsevier: Amsterdam, 1985; Chapter 8.
8. Patai, S., Rappoport, Z., Eds. The Chemistry of Organic Selenium and Tellurium Compounds; Wiley: New York, 1986; Vol. 1, Chapters 3 and 14.
9. Fujihara, H.; Takaguchi, Y.; Furukawa, N. Chem. Lett. 1992, 501.
10. (a) Gellatly, R. P.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1976, 913.
11. (b) Brieaddy, L. E.; Hurlbert, B. S.; Mehta, N. B. J. Org. Chem. 1981, 46, 1630.
12. 1H NMR spectral properties of the boat and chair forms. One of the conformers shows the nonequivalent methylenes as a distinct AB quartet due to rigidity of the conformer, while the other has a singlet or AB quartet with the small difference of chemical shifts for the methylene peak due to flexibility of the conformer. The former signals are assignable to the rigid chair conformer and the latter to the boat conformer. Such structural assignments were used and confirmed to be eligible for dibenzodithiocin 13 and its related compounds by Ollis et al. in the ref 8.
13. Fujihara, H.; Kawada, A.; Furukawa, N. Heterocycles 1986, 24, 17.
14. Ohkata, K.; Okada, K.; Akiba, K-Y. Heteroat. Chem. 1995, 6, 145.
15. (a) Detty, M. R. J. Org. Chem. 1980, 45, 274.
16. (b) Kobayashi, M.; Ohkubo, H.; Shimizu, T. Bull. Chem. Soc. Jpn. 1986, 59, 503.
17. Fujihara, H.; Mima, H.; Chiu, J.-J.; Furukawa, N. Tetrahedron Lett. 1990, 31, 2307.
18. Fujihara, H.; Uehara, T.; Erata, T.; Furukawa, N. Chem. Lett. 1993, 263.