2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF5 Groups: A Synthetic and Structural Study

Guoxiong Hua, Junyi Du, Alexandra M. Z. Slawin, J. Derek Woollins*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)
1 Downloads (Pure)

Abstract

A series of new 2,4-diaryl-1,3-chalcogen azoles having pentafluorosulfanyl SF5 functional groups has been prepared by means of the two-component cyclization of the selenoamide or thioamide with alpha-bromoketones. The selenoamides or thioamides were obtained from the reaction of Woollins' reagent or Lawesson's reagent with 4-pentafluorosulfanylbenzonitrile, followed by hydrolysis with water. All new compounds were characterised by H-1, C-13, Se-77, F-19 NMR spectroscopy and accurate mass measurement. X-ray crystal structure analysis of the selenoamide, thioamide and 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles reveal that the selenoamide and thioamide have very similar structural features along with similar intermolecular interactions such as the pi-pi stacking and the weak N-H center dot center dot center dot E (E = S or Se) hydrogen bonding. The 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles show the newly formed five-membered N(1)-C(2)-E(3)-C(4)-C(5) ring is either perfectly planar (and coplanar with two peripheral aryl ring planes) or near-planar. The pi-pi intermolecular interactions and the weak C-H center dot center dot center dot pi and C-H center dot center dot center dot X (X = Br, F, O) hydrogen bonding are discussed in the cases of 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles.

Original languageEnglish
Pages (from-to)3876-3886
Number of pages11
JournalThe Journal of Organic Chemistry
Volume79
Issue number9
DOIs
Publication statusPublished - 2 May 2014

Keywords

  • Hypervalent sulfur fluorides
  • X-ray
  • Primary selenoamides
  • Crystal-structure
  • Facile synthesis
  • 1,3-selenazol-4-one derivatives
  • Efficient synthesis
  • Organic-molecules
  • Haloacyl halides
  • Selenium

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