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

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]

The Covalent Linking of Organophosphorus Heterocycles to Date Palm Wood-Derived Lignin: Hunting for New Materials with Flame-Retardant Potential

“…We show that an interesting lignin can be obtained by subjecting date palm wood to butanosolv pretreatment, complementing previous work on this lignin type [31]. Through the use of 31 P NMR spectroscopy methods, a technique frequently used by Professor Woollins [32,33], this lignin was characterised before and after modification with the novel P-heterocycles. Our preliminary assessment of the flameretardant potential of the novel lignin-OPFR conjugates will guide future work in this developing research area.…”

“…technique frequently used by Professor Woollins [32,33], this lignin was characterised before and after modification with the novel P-heterocycles. Our preliminary assessment of the flame-retardant potential of the novel lignin-OPFR conjugates will guide future work in this developing research area.…”

Deoxygenation of chalcogen oxides EO2 (E = S, Se) with phosphaWittig reagents

“…Nevertheless, the formation of the mixed P-O/P-S cycles 4: Dip Ter, 5: Dip Ter and 6: Dip Ter is unusual (Figure S31). [78][79][80][81] Our attempts to rationally synthesize these systems failed 1) and the S species at 126.4 ppm.…”

Application of four-membered ring chalcogenation reagents to the synthesis of new phosphorus-chalcogen heterocycles

“…heterocycles are the four-membered ring compounds, Lawesson's reagent (LR, R = p-C 6 H 4 OMe), a highly efficient thionation reagent, 6-11 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide (FcLR, a ferrocene analogy of Lawesson's reagent), another alternatively efficient thionation reagent, [12][13][14][15][16] and 2,4-diphenyl-1,3-diselenadiphosphetane 2,4-diselenide [{PhP(Se)(µ-Se)} 2 ] (Woollins' reagent, WR, R = Ph, a selenium counterpart of Lawesson's reagent), as a highly efficient selenation reagent. [17][18][19][20][21][22][23][24][25] Very recently, we have reported these chalcogenation reagents used as efficient building blocks for the synthesis of a series of phosphorus-chalcogen macrocycles incorporating two phosphorus atoms and four chalcogen atoms [X 2 -P 2 -X 2 (X = O, S, Se)] in the central ring.…”