Rapid acyl migration between pyrogallyl 1,2- and 1,3-dipivaloates

Yaming Shan, Jimmy Liu, Nigam P. Rath, George W. Gokel

Research output: Contribution to journalArticle

1 Scopus citations

Abstract

Pyrogallol and its derivatives are biologically active compounds, and pyrogallol also forms the basis of an increasingly important tetrameric supramolecular scaffold. Pyrogallol[4]arenes are tetrameric macrocycles that form from 1,2,3-trihydroxybenzene and aldehydes under acidic conditions. Pyrogallol was treated with two equivalents of pivaloyl chloride to form pyrogallyl dipivaloate. A mixture of regioisomers was invariably obtained and a rapid equilibrium was observed between the 1,2- and 1,3-diesters in polar solvents. A pure sample of solid pyrogallyl 1,2-dipivaloate was isolated and its crystal structure was obtained. The pure compound was shown to rearrange to mixtures similar to those isolated initially.

Original languageEnglish (US)
Pages (from-to)333-336
Number of pages4
JournalNatural Product Communications
Volume7
Issue number3
DOIs
StatePublished - 2012
Externally publishedYes

Keywords

  • Acyl migration
  • Pivalic acid
  • Protecting group
  • Pyrogallol
  • Pyrogallol[4]arene
  • Solvent effect

ASJC Scopus subject areas

  • Pharmacology
  • Plant Science
  • Drug Discovery
  • Complementary and alternative medicine

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