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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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Date
03/07/2015
Author
Hua, Guoxiong
Du, Junyi
Woollins, J Derek
Surgenor, Brian Andrew
Slawin, Alexandra Martha Zoya
Funder
EPSRC
EPSRC
EPSRC
Grant ID
EP/K503940/1
EP/K031252/1
EP/K039210/1
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
QD Chemistry
DAS
Metadata
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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.
Citation
Hua , G , Du , J , Woollins , J D , Surgenor , B A & Slawin , A M Z 2015 , ' Novel fluorinated phosphorus–sulfur heteroatom compounds : synthesis and characterization of ferrocenyl- and aryl-phosphonofluorodithioic salts, adducts, and esters ' , Molecules , vol. 20 , no. 7 , pp. 12175-12197 . https://doi.org/10.3390/molecules200712175
Publication
Molecules
Status
Peer reviewed
DOI
https://doi.org/10.3390/molecules200712175
ISSN
1420-3049
Type
Journal article
Rights
© 2015 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
Collections
  • University of St Andrews Research
URL
http://www.mdpi.com/1420-3049/20/7/12175/s1
URI
http://hdl.handle.net/10023/6911

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