Photorearrangement of [8]-2,6-Pyridinophane N-Oxide

J Am Chem Soc. 2020 Dec 9;142(49):20717-20724. doi: 10.1021/jacs.0c09310. Epub 2020 Nov 23.

Abstract

Reaction pathways operative when pyridinophane N-oxides are photoirradiated have been studied using time course analyses and careful isolation of photolabile intermediates with support from DFT calculations. Based on the data and the isolation of two previously unknown heterocyclophanes, we outline a unified mechanistic scheme that explains competing processes under varying photochemical conditions.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aza Compounds / chemistry*
  • Aziridines / chemistry
  • Bridged-Ring Compounds / chemistry*
  • Density Functional Theory
  • Molecular Conformation
  • Oxides / chemistry
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry
  • Ultraviolet Rays*

Substances

  • Aza Compounds
  • Aziridines
  • Bridged-Ring Compounds
  • Oxides
  • Pyrroles
  • aziridine
  • 2,6-pyridinophane