Cycloreversion of azetidines via oxidative electron transfer. steady-state and time-resolved studies

Org Lett. 2008 Nov 20;10(22):5207-10. doi: 10.1021/ol802181u. Epub 2008 Oct 21.

Abstract

Cycloreversion of cis- and trans-1,2,3-triphenylazetidine (c-2 and t-2) is achieved by electron transfer to (tris(4-bromophenyl)aminium radical cation (5 (*+)). Stepwise C-N and C-C bond cleavage of azetidine radical cations leads to cis- and trans-stilbene, together with N-benzylideneaniline, as final products. Mechanistic evidence is provided by quenching studies, using laser flash photolysis to generate 5 (*+) from its neutral precursor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azetidines / chemistry*
  • Cyclization
  • Electron Transport
  • Organometallic Compounds / chemistry
  • Quaternary Ammonium Compounds / chemistry
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism
  • Time Factors

Substances

  • Azetidines
  • Organometallic Compounds
  • Quaternary Ammonium Compounds
  • tris(4-bromophenyl)ammoniumyl hexachloroantimonate
  • azetidine