Fusion of photochromic reaction and synthetic reaction: photoassisted cyclization to highly strained chiral azobenzenophanes

Org Lett. 2012 Jul 6;14(13):3252-5. doi: 10.1021/ol300992d. Epub 2012 Jun 13.

Abstract

A method for synthesizing highly strained cyclic structures by combining photochromic and synthetic reactions is described. Tightly linked azobenzene-binaphthyl dyads (R)-4 and (R)-6 could not be obtained by conventional cyclization, but continuous application of photoirradiation, which induced (E)→(Z) isomerization of the azobenzene moiety, allowed the cyclization reaction to proceed, affording the desired chiral azobenzenophanes.

MeSH terms

  • Azo Compounds / chemical synthesis*
  • Azo Compounds / chemistry
  • Cyclization
  • Molecular Structure
  • Photochemical Processes
  • Ultraviolet Rays

Substances

  • Azo Compounds
  • azobenzene