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.
Highlights
Organophosphorus-fluorine heteroatom compounds (OPFHACs) bearing a P–F bond are of interest due to their diverse chemical or biological activities, such as selective phosphorylating agents in synthesis, and efficient inhibition of several classes of enzyme [1,2,3,4,5,6,7,8,9,10,11,12]
We extend this procedure for the synthesis of potassium and tetrabutylammonium salts of ferrocenyl- and aryl-phosphonofluoridodithioates, and the related organic adducts and esters
FcLR reacted with two equivalents of fresh dry potassium fluoride in dry acetonitrile at 80 °C under N2 atmosphere for 1 h, giving rise to potassium ferrocenylphosphonofluoridodithioate 1 in 97% yield; or with two equivalents of tetrabutylammonium fluoride (TBAF) in tetrahydrofuran at room temperature for 1 h providing tetrabutylammonium ferrocenylphosphonofluoridodithioate 2 in 99% yield (Scheme 1)
Summary
Organophosphorus-fluorine heteroatom compounds (OPFHACs) bearing a P–F bond are of interest due to their diverse chemical or biological activities, such as selective phosphorylating agents in synthesis, and efficient inhibition of several classes of enzyme [1,2,3,4,5,6,7,8,9,10,11,12] This new class of thiophosphates bearing one or more anion FPS− units was first prepared from the reaction of alkali metal fluorides and P4S10 by Roesky’s group [13,14]. To the best of our knowledge, this is the first reported synthesis and characterization of ferrocenyl-phosphonofluorodithioates [FcPS2F]− and their structural analogues, providing a valuable addition to the library of phosphodithioate compounds
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