Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals. An experimental and theoretical study

G A DiLabio, K U Ingold, M D Roydhouse, J C Walton

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15 Citations (Scopus)

Abstract

Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals gave distinct EPR spectra thanks to surprisingly large beta-hydrogen atom hyperfine splittings that enabled them to be characterized and monitored. DFT computations indicated that the axial species (X = CH2) had a higher barrier to rotation about the (O)C-alpha-C-beta bond. The computed difference DeltaHdegrees for the axial and equatorial radicals (R = H, X CH2) was 0.8 kcal mol(-1).

Original languageEnglish
Pages (from-to)4319-4322
Number of pages4
JournalOrganic Letters
Volume6
DOIs
Publication statusPublished - 11 Nov 2004

Keywords

  • ELECTRON-SPIN-RESONANCE
  • CYCLOALKYLMETHYL RADICALS
  • PARAMAGNETIC RESONANCE
  • ACYL RADICALS
  • CONFORMATIONAL-ANALYSIS
  • ORGANIC-CHEMISTRY
  • CARBON-MONOXIDE
  • ALKYL RADICALS
  • SIGMA-RADICALS
  • ALLYLSTANNANES

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