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Novel fluorinated phosphorus–sulfur heteroatom compounds: synthesis and characterization of ferrocenyl- and aryl-phosphonofluorodithioic salts, adducts, and esters

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Guoxiong Hua, Junyi Du, J Derek Woollins, Brian Andrew Surgenor, Alexandra Martha Zoya Slawin

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Abstract

A series of novel ferrocenyl- and aryl-phosphonofluorodithioic salts, adducts, and esters has been prepared. The reaction of 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide {[FcP(μ-S)S]2, FcLR} with dry KF or tetrabutylammonium fluoride (TBAF) led to the corresponding potassium and tetrabutylammonium salts of ferrocenyldithiofluorophosphinic acids. Treating potassium ferrocenyldithiofluorophosphinic acid with an equimolar amount of tetraphenylphosphonium chloride readily yielded the corresponding organic adducts, and with mono- and di-halogenated alkanes generated a series of the corresponding esters of ferrocenylphosphonofluoridodithioates. Similarly, using 1,3-epithionaphtho[1,8-cd][1,2,6] oxadiphosphinine 1,3-disulfide or Belleau’s Reagent in place of FcLR resulted in the corresponding novel salts, adducts, and ester derivatives. All new compounds have been characterized by means of multi-NMR (1H, 13C, 31P, 19F) spectroscopy and accurate mass measurement in conjunction with single crystal X-ray crystallography of four structures.

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Original languageEnglish
Pages (from-to)12175-12197
JournalMolecules
Volume20
Issue number7
DOIs
StatePublished - 3 Jul 2015

    Research areas

  • 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane, 2,4-disulfide, Salts of phenyldithio- fluorophosphinic acids, Mono- and di-halogenated alkanes, Esters of phenylphosphono-fluoridodithioates

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