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Molecules 2015, 20(7), 12175-12197; doi:10.3390/molecules200712175

Novel Fluorinated Phosphorus–Sulfur Heteroatom Compounds: Synthesis and Characterization of Ferrocenyl- and Aryl-Phosphonofluorodithioic Salts, Adducts, and Esters

EaStCHEM School of Chemistry, University of St. Andrews, St Andrews, Fife KY16 9ST, UK
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Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 7 June 2015 / Revised: 27 June 2015 / Accepted: 30 June 2015 / Published: 3 July 2015
(This article belongs to the Section Organic Synthesis)
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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. View Full-Text
Keywords: 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 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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Hua, G.; Du, J.; Surgenor, B.A.; Slawin, A.M.Z.; Woollins, J.D. Novel Fluorinated Phosphorus–Sulfur Heteroatom Compounds: Synthesis and Characterization of Ferrocenyl- and Aryl-Phosphonofluorodithioic Salts, Adducts, and Esters. Molecules 2015, 20, 12175-12197.

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