Beilstein Journal of Organic Chemistry (Jul 2020)

Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

  • Csilla Hargitai,
  • Györgyi Koványi-Lax,
  • Tamás Nagy,
  • Péter Ábrányi-Balogh,
  • András Dancsó,
  • Gábor Tóth,
  • Judit Halász,
  • Angéla Pandur,
  • Gyula Simig,
  • Balázs Volk

DOI
https://doi.org/10.3762/bjoc.16.136
Journal volume & issue
Vol. 16, no. 1
pp. 1636 – 1648

Abstract

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Treatment of alkoxy-substituted o-(pivaloylaminomethyl)benzaldehydes under acidic conditions resulted in the formation of the regioisomeric aldehydes and/or dimer-like products. Detailed NMR studies and single-crystal X-ray measurements supported the structure elucidation of the compounds. DFT calculations were also carried out to clarify the reaction mechanism, and to explain the observed product distributions and structural variances in the dimer-like products. Studies on the transformation of unsubstituted o-(pivaloylaminomethyl)benzaldehyde under similar conditions were presented as well.

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