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

Authors

James K. Howard, University of Tasmania
Chintan Amin, California State University
Brendan Lainhart, California State University
Jason A. Smith, University of Tasmania
Jack Rimington, University of WollongongFollow
Christopher J. T Hyland, University of WollongongFollow

RIS ID

94384

Publication Details

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.

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.