Synthesis of methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate via a Hofmann rearrangement utilizing trichloroisocyanuric acid as an oxidant

J Org Chem. 2011 Jan 7;76(1):277-80. doi: 10.1021/jo101504e. Epub 2010 Dec 6.

Abstract

A trichloroisocyanuric acid (TCCA) mediated Hofmann rearrangement was utilized to synthesize methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate. A variety of functional groups are tolerated in this reaction including vinyl, cyclopropyl, pyridyl, aryl, benzyl, and nitro groups.

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Oxidants / chemistry*
  • Stereoisomerism
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / chemistry*

Substances

  • Oxidants
  • Vinyl Compounds
  • methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate