Heterocyclic rearrangements in constrained media. A zeolite-directed photorearrangement of 1,2,4-oxadiazoles

J Org Chem. 2005 Mar 18;70(6):2322-4. doi: 10.1021/jo047910+.

Abstract

[reaction: see text] The first intrazeolite-photoinduced rearrangement of a five-membered heterocycle is reported. A completely different behavior compared to solution irradiations has been observed. The zeolite's role in directing the photoreaction of 3-phenyl-1,2,4-oxadiazoles toward the formation of the corresponding 1,3,4-oxadiazoles in a ring contraction-ringexpansion route is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Models, Molecular
  • Molecular Structure
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / radiation effects
  • Photochemistry
  • Ultraviolet Rays
  • Zeolites / chemistry*

Substances

  • Oxadiazoles
  • Zeolites