Intramolecular homolytic substitution at tellurium: Preparation of a dihydrotellurophene by alkyltelluride-mediated S(RN)1/S(H)i reactions

Tetrahedron Letters

Volumn 38, Issue 48, 1997, Pages 8429-8432

  Laws, Melissa J ^a   Schiesser, Carl H ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; TELLURIUM; TELLURIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; OXIDATION; SYNTHESIS;

EID: 0030690115     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10239-8     Document Type: Article

References (17)

1. Lyons, J. E.; Schiesser, C. H.; Sutej, K., J. Org. Chem., 1993, 58, 5632.
2. Reactions involving sodium aryl-or alkyl-telluroates are sensitive to small quantities of oxygen. As organic ditellurides are easily removed by chromatography, we commonly add excess reagent in order to overcome these difficulties and provide maximum yields. See: Schiesser, C. H.; Skidmore, M. A., J. Chem. Soc. Perkin Trans. 1, 1997, (in press) and reference 4.
3. Petragnani, N., Tellurium in Organic Synthesis; Academic Press: London, 1994.
4. Lucas, M. A.; Schiesser, C. H., J. Org. Chem., 1996, 61, 5754.
5. The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1986.
6. RN1 Mechanism; American Chemical Society: Washington, DC, 1983. For recent examples, see: Nazareno, M. A.; Rossi, R. A., J. Org. Chem., 1996, 61, 1645. Beugelmans, R.; Chbani, M.; Soufiaoui, M., Tetrahedron Lett., 1996, 37, 1603. Harsanyi, M. C.; Lay, P. A.; Norris, R. K.; Witting, P. K., Aust. J. Chem., 1996, 49, 581. Gellis, A.; Vanelle, P.; Kaafarani, M.; Benakli, K.; Crozet, M. P., Tetrahedron, 1997, 53, 5471. Medebielle, M.; Pinson, J.; Saveant, J.-M., Electrochimica Acta, 1997, 42, 2049.
7. RN1 Mechanism; American Chemical Society: Washington, DC, 1983. For recent examples, see: Nazareno, M. A.; Rossi, R. A., J. Org. Chem., 1996, 61, 1645. Beugelmans, R.; Chbani, M.; Soufiaoui, M., Tetrahedron Lett., 1996, 37, 1603. Harsanyi, M. C.; Lay, P. A.; Norris, R. K.; Witting, P. K., Aust. J. Chem., 1996, 49, 581. Gellis, A.; Vanelle, P.; Kaafarani, M.; Benakli, K.; Crozet, M. P., Tetrahedron, 1997, 53, 5471. Medebielle, M.; Pinson, J.; Saveant, J.-M., Electrochimica Acta, 1997, 42, 2049.
8. RN1 Mechanism; American Chemical Society: Washington, DC, 1983. For recent examples, see: Nazareno, M. A.; Rossi, R. A., J. Org. Chem., 1996, 61, 1645. Beugelmans, R.; Chbani, M.; Soufiaoui, M., Tetrahedron Lett., 1996, 37, 1603. Harsanyi, M. C.; Lay, P. A.; Norris, R. K.; Witting, P. K., Aust. J. Chem., 1996, 49, 581. Gellis, A.; Vanelle, P.; Kaafarani, M.; Benakli, K.; Crozet, M. P., Tetrahedron, 1997, 53, 5471. Medebielle, M.; Pinson, J.; Saveant, J.-M., Electrochimica Acta, 1997, 42, 2049.
9. RN1 Mechanism; American Chemical Society: Washington, DC, 1983. For recent examples, see: Nazareno, M. A.; Rossi, R. A., J. Org. Chem., 1996, 61, 1645. Beugelmans, R.; Chbani, M.; Soufiaoui, M., Tetrahedron Lett., 1996, 37, 1603. Harsanyi, M. C.; Lay, P. A.; Norris, R. K.; Witting, P. K., Aust. J. Chem., 1996, 49, 581. Gellis, A.; Vanelle, P.; Kaafarani, M.; Benakli, K.; Crozet, M. P., Tetrahedron, 1997, 53, 5471. Medebielle, M.; Pinson, J.; Saveant, J.-M., Electrochimica Acta, 1997, 42, 2049.
10. RN1 Mechanism; American Chemical Society: Washington, DC, 1983. For recent examples, see: Nazareno, M. A.; Rossi, R. A., J. Org. Chem., 1996, 61, 1645. Beugelmans, R.; Chbani, M.; Soufiaoui, M., Tetrahedron Lett., 1996, 37, 1603. Harsanyi, M. C.; Lay, P. A.; Norris, R. K.; Witting, P. K., Aust. J. Chem., 1996, 49, 581. Gellis, A.; Vanelle, P.; Kaafarani, M.; Benakli, K.; Crozet, M. P., Tetrahedron, 1997, 53, 5471. Medebielle, M.; Pinson, J.; Saveant, J.-M., Electrochimica Acta, 1997, 42, 2049.
11. RN1 Mechanism; American Chemical Society: Washington, DC, 1983. For recent examples, see: Nazareno, M. A.; Rossi, R. A., J. Org. Chem., 1996, 61, 1645. Beugelmans, R.; Chbani, M.; Soufiaoui, M., Tetrahedron Lett., 1996, 37, 1603. Harsanyi, M. C.; Lay, P. A.; Norris, R. K.; Witting, P. K., Aust. J. Chem., 1996, 49, 581. Gellis, A.; Vanelle, P.; Kaafarani, M.; Benakli, K.; Crozet, M. P., Tetrahedron, 1997, 53, 5471. Medebielle, M.; Pinson, J.; Saveant, J.-M., Electrochimica Acta, 1997, 42, 2049.
12. Crich, D.; Chen. C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I., J. Am. Chem. Soc., 1994, 116, 8937.
13. Beckwith, A. L. J.; Palacios, S. M., J. Phys. Org. Chem., 1991, 4, 404.
14. The concentration of tetrahydrofuran is approximately 12M based on a density of 0.886 (25°).
15. Landolt-Börnstein, Numerical Data and Functional Relationships in Science and Technology, Vol II/18, Fischer, H., Ed.; Springer-Verlag: Berlin, 1994.
16. Schiesser, C. H.; Wild, L. M., Tetrahedron, 1996, 52, 13265.
17. Schiesser, C. H.; Zugaro, L. M., unpublished.