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

Molecules. 2017 Oct 10;22(10):1687. doi: 10.3390/molecules22101687.

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.

Keywords: 2,4-Diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide; diols; iodine oxidation; one-pot reaction; phosphorus-sulfur heterocycles.

MeSH terms

  • Crystallization
  • Ethylamines / chemistry
  • Heterocyclic Compounds / chemical synthesis*
  • Magnetic Resonance Spectroscopy / methods
  • Mass Spectrometry / methods
  • Metallocenes / chemistry
  • Molecular Structure
  • Organothiophosphorus Compounds / chemistry
  • Oxidation-Reduction
  • Phosphorus / chemistry*
  • Sulfur / chemistry*

Substances

  • Ethylamines
  • Heterocyclic Compounds
  • Metallocenes
  • Organothiophosphorus Compounds
  • Phosphorus
  • Sulfur
  • 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
  • triethylamine