A systematic 125Te NMR study of organotellurium compounds: The effect of oxidation states and substituents

Tetrahedron

Volumn 55, Issue 9, 1999, Pages 2545-2552

  Saito, Shinichi ^a,b   Zhang, Jian ^a   Tanida, Kyoko ^a   Takahashi, Shigemasa ^a   Koizumi, Toru ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

125Te NMR; Electronic effects; Organotellurium compounds

Indexed keywords

HALOOXATELLURANE DERIVATIVE; ORGANOTELLURIUM DERIVATIVE; TELLURANE; TELLURIDE; TELLURIUM 125; TELLURONIUM SALT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE IMAGING; ORGANIC CHEMISTRY; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 0033605192     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00040-X     Document Type: Article

References (23)

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4. (a) Zumbulyadis, N.; Gysling, H. J. J. Organomet. Chem. 1980, 192, 183-188. (b) McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Dalton, 1973, 2416-2418. (c) Kohne, B.; Lohner, W.; Praefcke, K.; Jakobsen, H. J.; Villadsen, B. J. Organomet. Chem. 1979, 166, 373-377. (d) Gombler, W. Z. Naturforsch. 1980,36B, 535-543. (e) Denny, D. B.; Denny, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347. (f) Chadha, R. K., Miller, J. M. Can. J. Chem. 1982, 60, 2256-2258. (g) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 7529-7539. (h) Jones, C. H. W.; Sharma, R. D.; Taneja, S. P. Can. J. Chem. 1986, 64, 980-986. (i) Detty, M. R.; Lenhart, W. C.; Gassman, P. G.; Callstrom, M. R. Organometallics, 1989, 8, 861-865. (j) Shimizu, T.; Urakubo, T.; Kamigata, N. J. Org. Chem. 1996, 61, 8032-8038. (k) Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. A. 1997, 101, 4121-4127.
5. (a) Zumbulyadis, N.; Gysling, H. J. J. Organomet. Chem. 1980, 192, 183-188. (b) McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Dalton, 1973, 2416-2418. (c) Kohne, B.; Lohner, W.; Praefcke, K.; Jakobsen, H. J.; Villadsen, B. J. Organomet. Chem. 1979, 166, 373-377. (d) Gombler, W. Z. Naturforsch. 1980,36B, 535-543. (e) Denny, D. B.; Denny, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347. (f) Chadha, R. K., Miller, J. M. Can. J. Chem. 1982, 60, 2256-2258. (g) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 7529-7539. (h) Jones, C. H. W.; Sharma, R. D.; Taneja, S. P. Can. J. Chem. 1986, 64, 980-986. (i) Detty, M. R.; Lenhart, W. C.; Gassman, P. G.; Callstrom, M. R. Organometallics, 1989, 8, 861-865. (j) Shimizu, T.; Urakubo, T.; Kamigata, N. J. Org. Chem. 1996, 61, 8032-8038. (k) Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. A. 1997, 101, 4121-4127.
6. (a) Zumbulyadis, N.; Gysling, H. J. J. Organomet. Chem. 1980, 192, 183-188. (b) McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Dalton, 1973, 2416-2418. (c) Kohne, B.; Lohner, W.; Praefcke, K.; Jakobsen, H. J.; Villadsen, B. J. Organomet. Chem. 1979, 166, 373-377. (d) Gombler, W. Z. Naturforsch. 1980,36B, 535-543. (e) Denny, D. B.; Denny, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347. (f) Chadha, R. K., Miller, J. M. Can. J. Chem. 1982, 60, 2256-2258. (g) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 7529-7539. (h) Jones, C. H. W.; Sharma, R. D.; Taneja, S. P. Can. J. Chem. 1986, 64, 980-986. (i) Detty, M. R.; Lenhart, W. C.; Gassman, P. G.; Callstrom, M. R. Organometallics, 1989, 8, 861-865. (j) Shimizu, T.; Urakubo, T.; Kamigata, N. J. Org. Chem. 1996, 61, 8032-8038. (k) Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. A. 1997, 101, 4121-4127.
7. (a) Zumbulyadis, N.; Gysling, H. J. J. Organomet. Chem. 1980, 192, 183-188. (b) McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Dalton, 1973, 2416-2418. (c) Kohne, B.; Lohner, W.; Praefcke, K.; Jakobsen, H. J.; Villadsen, B. J. Organomet. Chem. 1979, 166, 373-377. (d) Gombler, W. Z. Naturforsch. 1980,36B, 535-543. (e) Denny, D. B.; Denny, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347. (f) Chadha, R. K., Miller, J. M. Can. J. Chem. 1982, 60, 2256-2258. (g) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 7529-7539. (h) Jones, C. H. W.; Sharma, R. D.; Taneja, S. P. Can. J. Chem. 1986, 64, 980-986. (i) Detty, M. R.; Lenhart, W. C.; Gassman, P. G.; Callstrom, M. R. Organometallics, 1989, 8, 861-865. (j) Shimizu, T.; Urakubo, T.; Kamigata, N. J. Org. Chem. 1996, 61, 8032-8038. (k) Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. A. 1997, 101, 4121-4127.
8. (a) Zumbulyadis, N.; Gysling, H. J. J. Organomet. Chem. 1980, 192, 183-188. (b) McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Dalton, 1973, 2416-2418. (c) Kohne, B.; Lohner, W.; Praefcke, K.; Jakobsen, H. J.; Villadsen, B. J. Organomet. Chem. 1979, 166, 373-377. (d) Gombler, W. Z. Naturforsch. 1980,36B, 535-543. (e) Denny, D. B.; Denny, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347. (f) Chadha, R. K., Miller, J. M. Can. J. Chem. 1982, 60, 2256-2258. (g) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 7529-7539. (h) Jones, C. H. W.; Sharma, R. D.; Taneja, S. P. Can. J. Chem. 1986, 64, 980-986. (i) Detty, M. R.; Lenhart, W. C.; Gassman, P. G.; Callstrom, M. R. Organometallics, 1989, 8, 861-865. (j) Shimizu, T.; Urakubo, T.; Kamigata, N. J. Org. Chem. 1996, 61, 8032-8038. (k) Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. A. 1997, 101, 4121-4127.
9. (a) Zumbulyadis, N.; Gysling, H. J. J. Organomet. Chem. 1980, 192, 183-188. (b) McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Dalton, 1973, 2416-2418. (c) Kohne, B.; Lohner, W.; Praefcke, K.; Jakobsen, H. J.; Villadsen, B. J. Organomet. Chem. 1979, 166, 373-377. (d) Gombler, W. Z. Naturforsch. 1980,36B, 535-543. (e) Denny, D. B.; Denny, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347. (f) Chadha, R. K., Miller, J. M. Can. J. Chem. 1982, 60, 2256-2258. (g) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 7529-7539. (h) Jones, C. H. W.; Sharma, R. D.; Taneja, S. P. Can. J. Chem. 1986, 64, 980-986. (i) Detty, M. R.; Lenhart, W. C.; Gassman, P. G.; Callstrom, M. R. Organometallics, 1989, 8, 861-865. (j) Shimizu, T.; Urakubo, T.; Kamigata, N. J. Org. Chem. 1996, 61, 8032-8038. (k) Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. A. 1997, 101, 4121-4127.
10. (a) Zumbulyadis, N.; Gysling, H. J. J. Organomet. Chem. 1980, 192, 183-188. (b) McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Dalton, 1973, 2416-2418. (c) Kohne, B.; Lohner, W.; Praefcke, K.; Jakobsen, H. J.; Villadsen, B. J. Organomet. Chem. 1979, 166, 373-377. (d) Gombler, W. Z. Naturforsch. 1980,36B, 535-543. (e) Denny, D. B.; Denny, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347. (f) Chadha, R. K., Miller, J. M. Can. J. Chem. 1982, 60, 2256-2258. (g) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 7529-7539. (h) Jones, C. H. W.; Sharma, R. D.; Taneja, S. P. Can. J. Chem. 1986, 64, 980-986. (i) Detty, M. R.; Lenhart, W. C.; Gassman, P. G.; Callstrom, M. R. Organometallics, 1989, 8, 861-865. (j) Shimizu, T.; Urakubo, T.; Kamigata, N. J. Org. Chem. 1996, 61, 8032-8038. (k) Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. A. 1997, 101, 4121-4127.
11. (a) Zumbulyadis, N.; Gysling, H. J. J. Organomet. Chem. 1980, 192, 183-188. (b) McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Dalton, 1973, 2416-2418. (c) Kohne, B.; Lohner, W.; Praefcke, K.; Jakobsen, H. J.; Villadsen, B. J. Organomet. Chem. 1979, 166, 373-377. (d) Gombler, W. Z. Naturforsch. 1980,36B, 535-543. (e) Denny, D. B.; Denny, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347. (f) Chadha, R. K., Miller, J. M. Can. J. Chem. 1982, 60, 2256-2258. (g) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 7529-7539. (h) Jones, C. H. W.; Sharma, R. D.; Taneja, S. P. Can. J. Chem. 1986, 64, 980-986. (i) Detty, M. R.; Lenhart, W. C.; Gassman, P. G.; Callstrom, M. R. Organometallics, 1989, 8, 861-865. (j) Shimizu, T.; Urakubo, T.; Kamigata, N. J. Org. Chem. 1996, 61, 8032-8038. (k) Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. A. 1997, 101, 4121-4127.
12. (a) Zumbulyadis, N.; Gysling, H. J. J. Organomet. Chem. 1980, 192, 183-188. (b) McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Dalton, 1973, 2416-2418. (c) Kohne, B.; Lohner, W.; Praefcke, K.; Jakobsen, H. J.; Villadsen, B. J. Organomet. Chem. 1979, 166, 373-377. (d) Gombler, W. Z. Naturforsch. 1980,36B, 535-543. (e) Denny, D. B.; Denny, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347. (f) Chadha, R. K., Miller, J. M. Can. J. Chem. 1982, 60, 2256-2258. (g) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 7529-7539. (h) Jones, C. H. W.; Sharma, R. D.; Taneja, S. P. Can. J. Chem. 1986, 64, 980-986. (i) Detty, M. R.; Lenhart, W. C.; Gassman, P. G.; Callstrom, M. R. Organometallics, 1989, 8, 861-865. (j) Shimizu, T.; Urakubo, T.; Kamigata, N. J. Org. Chem. 1996, 61, 8032-8038. (k) Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. A. 1997, 101, 4121-4127.
13. Takahashi, T.; Zhang, J.; Kurose, N.; Takahashi, S.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1996, 7, 2797-2800.
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17. Dean, P. A. W.; Manivannan, V.; Vittal, J. J.; Inorg. Chem. 1989, 28, 2360-2368.
18. On the other hand, no coupling between the fluorine atom and the selenium atom of a fluorooxaselenurane was observed (ref. 8). These results indicate that the rate of the halogen exchange reaction of a halooxaselenurane is much faster compared to that of a halooxatellurane.
19. Saito, S.; Zhang, J.; Koizumi, T. J. Org. Chem. 1998, 63, 6029-6030.
20. A similar result has been reported for trichlorotelluranes (ref. 2f).
21. 77Se NMR of highly ionic halooxaselenuranes (ref. 8).
22. The electronegativity values were collected from Isaacs, N. S. Physical Organic Chemistry; Longman Scientific & Technical: Harlow, 1987; p. 31.
23. We think that the resonance structures B and C have more important contribution than the resonance structures D and E, since a larger coupling constant between the Te atom and F atom was observed when an electron-donating group was attached to the benzene ring of the fluorooxatelluranes (Table 1, entries 4-6).