Photochemical synthesis and properties of 1,6- and 1,8-naphthalenophanes

Molecules. 2013 Jan 21;18(1):1314-24. doi: 10.3390/molecules18011314.

Abstract

Various 1,6- and 1,8-naphthalenophanes were synthesized by using the Photo-Dehydro-Diels-Alder (PDDA) reaction of bis-ynones. These compounds are easily accessible from ω-(3-iodophenyl)carboxylic acids in three steps. The obtained naphthalenophanes are axially chiral and the activation barrier for the atropisomerization could be determined in some cases by means of dynamic NMR (DNMR) and/or dynamic HPLC (DHPLC) experiments.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Cycloaddition Reaction
  • Iodobenzoates / chemistry
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Photochemical Processes*
  • Propionates / chemistry
  • Stereoisomerism

Substances

  • Iodobenzoates
  • Naphthalenes
  • Propionates
  • 3-iodobenzoic acid