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Synthesis of nitrogen-substituted methylenecyclopropanes by strain-driven overman rearrangement of cyclopropenylmethyl trichloroacetimidates

Journal Article


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Abstract


  • Nitrogen-substituted methylenecyclopropanes have been prepared by a strain-driven Overman rearrangement of cyclopropenylmethyl trichloroacetimidates. The reaction proceeds at room temperature and without the need of a transition-metal catalyst. Furthermore, it has been shown that C-3-substituted cyclopropenylmethyl trichloroacetimidates undergo a hydrolytic ring-opening reaction to form allenylcarbinols.

UOW Authors


  •   Howard, James K. (external author)
  •   Amin, Chintan (external author)
  •   Lainhart, Brendan (external author)
  •   Smith, Jason A. (external author)
  •   Rimington, Jack (external author)
  •   Hyland, Christopher

Publication Date


  • 2014

Citation


  • Howard, J. K., Amin, C., Lainhart, B., Smith, J. A., Rimington, J. & Hyland, C. J. T. (2014). Synthesis of nitrogen-substituted methylenecyclopropanes by strain-driven overman rearrangement of cyclopropenylmethyl trichloroacetimidates. Journal of Organic Chemistry, 79 (17), 8462-8468.

Scopus Eid


  • 2-s2.0-84924325911

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3332&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2314

Number Of Pages


  • 6

Start Page


  • 8462

End Page


  • 8468

Volume


  • 79

Issue


  • 17

Abstract


  • Nitrogen-substituted methylenecyclopropanes have been prepared by a strain-driven Overman rearrangement of cyclopropenylmethyl trichloroacetimidates. The reaction proceeds at room temperature and without the need of a transition-metal catalyst. Furthermore, it has been shown that C-3-substituted cyclopropenylmethyl trichloroacetimidates undergo a hydrolytic ring-opening reaction to form allenylcarbinols.

UOW Authors


  •   Howard, James K. (external author)
  •   Amin, Chintan (external author)
  •   Lainhart, Brendan (external author)
  •   Smith, Jason A. (external author)
  •   Rimington, Jack (external author)
  •   Hyland, Christopher

Publication Date


  • 2014

Citation


  • Howard, J. K., Amin, C., Lainhart, B., Smith, J. A., Rimington, J. & Hyland, C. J. T. (2014). Synthesis of nitrogen-substituted methylenecyclopropanes by strain-driven overman rearrangement of cyclopropenylmethyl trichloroacetimidates. Journal of Organic Chemistry, 79 (17), 8462-8468.

Scopus Eid


  • 2-s2.0-84924325911

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3332&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2314

Number Of Pages


  • 6

Start Page


  • 8462

End Page


  • 8468

Volume


  • 79

Issue


  • 17