Hexamethylenetetramine–Bromine: A Novel Reagent for Selective Regeneration of Carbonyl Compounds from Oximes and Tosylhydrazones†‡

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

Babasaheb P. Bandgar, Shivaji B. Admane and Sandip S. Jare


Abstract

Hexamethylenetetramine–bromine (HMTAB) has been found to be an efficient and selective reagent for the mild oxidative cleavage of the C[double bond, length as m-dash]N of oximes and tosylhydrazones to yield their corresponding carbonyl compounds in good to excellent yields under mild conditions.


References

  1. Y. H. Kim, J. C. Jung and K. S. Kim, Chem. Ind., 1992, 31 Search PubMed and references cited therein.
  2. S. R. Sandler and W. Karo, Organic Functional Group Preparations, Academic Press, London, 1989, p. 430 Search PubMed; T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991 Search PubMed.
  3. G. W. Kabalka, R. D. Pace and P. P. Wadgaonkar, Synth. Commun., 1990, 20, 2453 CAS and references cited therein.
  4. R. E. Donaldson, J. C. Saddler, S. Byrn, A. T. Mckenzie and P. L. Fuch, J. Org. Chem., 1983, 48, 2167 CrossRef CAS and references cited therein.
  5. J. C. Lee, K. H. Kwak and J. P. Hwang, Tetrahedron Lett., 1990, 31, 6677 CrossRef CAS; B. Tamani and N. Goudarizian, Eur. Polym. J., 1992, 28, 1035 CrossRef CAS.
  6. D. P. Curran, J. F. Brill and D. M. Rakiewicz, J. Org. Chem., 1984, 49, 1654 CrossRef CAS; J. Drabowicz, Synthesis, 1990, 125; E. J. Corey, P. B. Hopkines, S. Kim, S. Yoo, K. P. Nambiar and J. R. Falk, J. Am. Chem. Soc., 1979, 101, 7131 CrossRef CAS.
  7. P. Laszlo and E. Polla, Synthesis, 1985, 439 CrossRef CAS.
  8. G. A. Olah, Q. Liao, C. S. Lee and G. K. Suryaprakash, Synlett, 1993, 427 CrossRef CAS.
  9. R. Joseph, A. Sudalai and T. Ravindranthan, Tetrahedron Lett., 1994, 35, 5493 CrossRef CAS; P. Kumar, V. R. Hegde, B. Pandey and T. Ravindranathan, J. Chem. Soc., Chem. Commun., 1993, 1553 RSC.
  10. N. B. Barhate, A. S. Gajare, R. D. Wakharkar and A. Sudalai, Tetrahedron Lett., 1997, 38, 635 CrossRef CAS.
  11. D. H. R. Barton, D. J. Lester and S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 1980, 1212 RSC.
  12. I. Yavari and A. Shaabani, J. Chem. Res. (S), 1994, 274 Search PubMed.
  13. For a review of positive halogens, see A. Foucaud, Chem. Halides, Pseudo-halides, Azides, 1983, 1, 441 Search PubMed.
  14. S. Kondo, M. Ohira, S. Kawasoe, H. Kunisada and Y. Yuki, J. Org. Chem., 1993, 58, 5003 CrossRef CAS.
  15. F. Minisci, E. Vismara, F. Fontana, E. Platone and J. Faraci, J. Chem. Soc., Perkin Trans. 2, 1989, 123 RSC.
  16. L. K. Blair, S. Hobbs, N. Bagnoli, L. Husband and N. Badika, J. Org. Chem., 1992, 57, 1600 CrossRef CAS.
  17. R. E. Banks, S. N. Mohialdin-Khaffaf, G. S. Lal, I. Sharif and R. G. Syvert, J. Chem. Soc., Chem. Commun., 1992, 595 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.