• Media type: E-Article
  • Title: Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner–Wadsworth–Emmons reaction
  • Contributor: Iakobson, George; Beier, Petr
  • Published: Beilstein Institut, 2012
  • Published in: Beilstein Journal of Organic Chemistry, 8 (2012), Seite 1185-1190
  • Language: English
  • DOI: 10.3762/bjoc.8.131
  • ISSN: 1860-5397
  • Keywords: Organic Chemistry
  • Origination:
  • Footnote:
  • Description: <jats:p>Diethyl 2-nitro-(pentafluorosulfanyl)benzylphosphonates, available by the vicarious nucleophilic substitution reaction of <jats:italic>meta-</jats:italic> and <jats:italic>para-</jats:italic>nitro-(pentafluorosulfanyl)benzenes and diethyl chloromethylphosphonate, undergo Horner–Wadsworth–Emmons reaction with aldehydes in the presence of potassium hydroxide in acetonitrile at ambient temperature to give (<jats:italic>E</jats:italic>)-2-nitro-1-alkenyl-(pentafluorosulfanyl)benzenes in good yields and high stereoselectivities. Follow-up transformations of the primary products provided (<jats:italic>E</jats:italic>)-1-alkenyl-(pentafluorosulfanyl)benzenes and 2-(2-arylethyl)-(pentafluorosulfanyl)anilines.</jats:p>
  • Access State: Open Access