Preparation and Thermal Decomposition of N,N'-Diacyl-N,N'-Dialkoxyhydrazines: Synthetic Applications and Mechanistic Insights Academic Article uri icon


  • Oxidation of various O-alkyl hydroxamates 1 where R1was a keto-methoxime, benzoyl, aryl, or alkyl group with ceric ammonium nitrate (CAN) or nickel peroxide (NiO2•H2O) leads to the corresponding esters in high yield. This augurs well for the facile synthesis of highly hindered esters. Dimers of type 2 were identified as intermediates in these oxidations, and a combination of experimental and theoretical results suggest that these dimers decompose in a stepwise 1,1-elimination manner via intermediate nitrenes to furnish the esters and not via a stepwise 1,2-elimination sequence as previously thought. © 1995, American Chemical Society. All rights reserved.

published proceedings

  • Journal of the American Chemical Society

author list (cited authors)

  • De Almeida, M. V., Barton, D., Bytheway, I., Ferreira, J. A., Hall, M. B., Liu, W., Taylor, D. K., & Thomson, L

citation count

  • 58

complete list of authors

  • De Almeida, Mauro V||Barton, Derek HR||Bytheway, Ian||Ferreira, J Albert||Hall, Michael B||Liu, Wansheng||Taylor, Dennis K||Thomson, Lisa

publication date

  • May 1995