Rapid and precise preparation of reactive benzeneselenolate solutions by reduction of diphenyl diselenide with hydrazine–sodium methanolate

(Note: The full text of this document is currently only available in the PDF Version )

Lars Henriksen and Nicolai Stuhr-Hansen


Abstract

Solutions of sodium benzeneselenolate sufficiently reactive to effect aromatic substitution and ester dealkylation are prepared in DMSO or NMP from diphenyl diselenide and hydrazine hydrate by titration with methanolic sodium methanolate.


References

  1. R. Monahan, D. Brown, L. Waykole and D. Liotta, in Organoselenium Chemistry, ed. D. Liotta, John Wiley & Sons, New York, 1987, ch. 4 Search PubMed.
  2. D. L. Klayman, in Organic Selenium Compounds, eds. D. L. Klayman and W. H. H. Günther, John Wiley & Sons, New York, 1973, p. 71, 96 Search PubMed.
  3. (a) B. Sjögren and S. Herdevall, Acta Chem. Scand., 1958, 12, 1347; (b) K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697 CrossRef CAS.
  4. (a) D. Liotta, W. Markiewick and H. Santisteban, Tetrahedron Lett., 1977, 50, 4365 CrossRef; (b) D. Liotta, U. Sunay, H. Santisteban and W. Markiewick, J. Org. Chem., 1981, 46, 2605 CrossRef CAS.
  5. P. Dowd and P. Kennedy, Synth. Commun., 1981, 11, 935 CAS.
  6. L. Syper and J. Mlochowski, Synthesis, 1984, 439 CrossRef CAS.
  7. H. Eggert, O. Nielsen and L. Henriksen, J. Am. Chem. Soc., 1986, 108, 1725 CrossRef CAS.
  8. L. Henriksen and N. Stuhr-Hansen, Synth. Commun., 1996, 26, 1897 CAS.
  9. H. J. Christau, B. Chabaud, R. Labaudiniere and H. Christol, Organometallics, 1985, 4, 657 CrossRef.
  10. (a) C. Degrand, J. Org. Chem., 1987, 52, 1421 CrossRef CAS; (b) C. Degrand, R. Prest and M. Nour, Phosphorus Sulfur, Relat. Elem., 1988, 38, 201 Search PubMed.
  11. A. B. Pierini and R. A. Rossi, J. Org. Chem., 1979, 44, 4667 CrossRef CAS.
  12. L. Engman and D. Stern, J. Org. Chem., 1994, 59, 5179 CrossRef CAS.
  13. C. J. Degrand, J. Chem. Soc., Chem. Commun., 1986, 1113 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.