Phosphorus-sulfur heterocycles incorporating an O-P(S)-O or O-P(S)-S-S-P(S)-O scaffold: one-pot synthesis and crystal structure study

Guoxiong Hua, Kate Davidson, David B. Cordes, Junyi Du, Alexandra M. Z. Slawin, J. Derek Woollins

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A new one-pot preparative route was developed to synthesize novel organophosphorus sulfur heterocycles via the reaction of the four-membered ring thionation reagent [2,4-diferrocenyl 1,3,2,4-diathiadiphosphetane 2,4-disulfide (FcLR, a ferrocene analogue of Lawesson’s reagent)] and alkenyl/aryl-diols and I2 (or SOCl2) in the presence of triethylamine. Therefore, a series of five- to ten-membered heterocycles bearing an O-P(S)-O or an O-P(S)-S-S-P(S)-O linkage were synthesized. The synthesis features a novel application of the multicomponent reaction, providing an efficient and environmentally benign method for the preparation of the unusual phosphorus-sulfur heterocycles. Seven representative X-ray structures confirm the formation of these heterocycles.
Original languageEnglish
Article number1687
Number of pages14
JournalMolecules
Volume22
Issue number10
DOIs
Publication statusPublished - 10 Oct 2017

Keywords

  • 2,4-Diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide
  • Diols
  • One-pot reaction
  • Iodine oxidation
  • Phosphorus-sulfur heterocycles

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