Kinetic control wins out over thermodynamic control in Friedel-Crafts acyl rearrangements

Tahani Mala'bi, Sergey Pogodin, Israel Agranat*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

1,5-, 1,8- and 9,10-diacetylanthracenes undergo Friedel-Crafts acyl rearrangements in polyphosphoric acid at 130-150 °C to give 3-methylbenz[de]anthracen-1-one via the kinetically-controlled 1,9-diacetylanthracene. The rearrangement mechanism is supported by DFT calculations of diacetylanthracenes, their σ-complexes, O-protonates, and O,O-diprotonates. The importance of kinetic control versus thermodynamic control in Friedel-Crafts acyl rearrangements is highlighted. Certain features of reversibility are also suggested.

Original languageEnglish
Pages (from-to)1854-1857
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number16
DOIs
StatePublished - 20 Apr 2011

Keywords

  • DFT calculations
  • Diacetylanthracenes
  • Polyphosphoric acid
  • Rearrangement mechanism
  • Reversibility

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