Selective and Sequential Aminolysis of Benzotrifuranone: Synergism of Electronic Effects and Ring Strain Gradient.

  title={Selective and Sequential Aminolysis of Benzotrifuranone: Synergism of Electronic Effects and Ring Strain Gradient.},
  author={Matthew B. Baker and Renan B. Ferreira and Jonathan Tasseroul and Andrew J. Lampkins and Alexandre Al Abbas and Khalil A. Abboud and Ronald K. Castellano},
  journal={The Journal of organic chemistry},
  volume={81 19},
Benzotrifuranone (BTF), bearing three symmetry-equivalent lactone rings, is unique in its ability to undergo highly selective and sequential aminolysis reactions in one-pot to afford multifunctionalized molecules (>80% overall yield). New insight into this behavior is presented through kinetics measurements (by stopped-flow IR spectroscopy), X-ray crystal structure analysis, quantum chemical calculations, and comparison of BTF to other benzoate esters, including its ring expanded congener… 
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  • I. Um, A. Bae
  • Chemistry
    The Journal of organic chemistry
  • 2011
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