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

• Published in: Molecules (Basel, Switzerland) Vol. 22; no. 10; p. 1687
• Main Authors: Hua, Guoxiong, Davidson, Kate, Cordes, David B, Du, Junyi, Slawin, Alexandra M Z, Woollins, J Derek
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 10.10.2017; MDPI
• Subjects: 2,4-Diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide; Aromatic compounds; Crystal structure; Crystallization; Diols; Ethylamines - chemistry; Heterocyclic Compounds - chemical synthesis; Iodine; iodine oxidation; Magnetic Resonance Spectroscopy - methods; Mass Spectrometry - methods; Metallocenes - chemistry; Molecular Structure; one-pot reaction; Organothiophosphorus Compounds - chemistry; Oxidation-Reduction; Phosphorus; Phosphorus - chemistry; phosphorus-sulfur heterocycles; Reagents; Single crystals; Solvents; Sulfur; Sulfur - chemistry; Triethylamine; one-pot reaction; diols; phosphorus-sulfur heterocycles; 2,4-Diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide; iodine oxidation
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules22101687

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.