Photochemical double 5-exo cyclization of alkenyl-substituted dithienylacetylenes: efficient synthesis of diarylated dithienofulvalenes

Angew Chem Int Ed Engl. 2013 Sep 27;52(40):10519-23. doi: 10.1002/anie.201303738. Epub 2013 Aug 13.

Abstract

Smooth and selective: Upon photoirradiation, bis(3-alkenyl-2-thienyl)acetylenes smoothly and selectively undergo double 5-exo-dig cyclization to produce a series of thiophene-fused pentafulvalenes with various aryl substituents. In this fused π-conjugated skeleton, the fused thiophene rings and the aryl substituents significantly modulate the electronic structure of the pentafulvalene skeleton.

Keywords: cyclization; pentafulvalene; photoreaction; redox properties; π conjugation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Benzene Derivatives / chemistry*
  • Cyclization
  • Cyclopentanes / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Photochemical Processes
  • Photochemistry / methods*

Substances

  • Alkynes
  • Benzene Derivatives
  • Cyclopentanes
  • fulvene