- Room-temperature reduction of sulfur hexafluoride with metal phosphides
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Upon treatment with sulfur hexafluoride, alkali metal diphenyl or dicyclohexyl phosphides are oxidized within seconds to tetraphenyl or tetracyclohexyl diphosphines. When bulky di-tert-butylphosphide is employed, fluorophosphine intermediates are detected. This is the first reported reaction of sulfur hexafluoride with metal phosphides, and a rare example of reactivity of sulfur hexafluoride at ambient temperature. This journal is
- Huchenski, Blake S. N.,Speed, Alexander W. H.
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supporting information
p. 7128 - 7131
(2021/07/28)
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- Bismuth(iii) Thiophosphinates: Understanding How a Small Atomic Change Influences Antibacterial Activity and Mammalian Cell Viability
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Diphenylphosphinothioic acid (HSP(=O)Ph2) and diphenylphosphinodithioic acid (HSP(=S)Ph2) have been used to synthesise four BiIII complexes: 1 [Bi(SP(=O)Ph2)3], 2 [BiPh(SP(=O)Ph2)2], 3 [BiPh2(SP(=O)Ph2)], and 4 [Bi(SP(=S)Ph2)3], using BiPh3 and [Bi(OtBu)3] as bismuth sources. The complexes have been characterised by NMR spectroscopy, mass spectrometry, infrared spectroscopy, powder X-ray diffraction, and singe crystal X-ray crystallography (2-4). Biological studies indicated that despite complexes 2 and 3 reducing mammalian cell viability, their antibacterial activity provides a good degree of selectivity towards both Gram positive and Gram negative bacterial strains. The minimum inhibitory concentrations for complexes 2 and 3 are in the range of 0.52-5.5 μM towards the bacteria tested. Homoleptic complexes 1 and 4 were generally less active towards both bacterial and mammalian cells.
- Senevirathna, Dimuthu C.,Duffin, Rebekah N.,Stephens, Liam J.,Herdman, Megan E.,Werrett, Melissa V.,Andrews, Philip C.
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p. 1226 - 1236
(2020/10/07)
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- Benign and high-yielding, large-scale synthesis of diphenylphosphinodithioic acid and related compounds
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Diphenylphosphinodithioic acid (6b) and its triethyl ammonium salt (6a) were prepared by two new synthetic pathways, each employing cheap and readily available starting materials. These facile one-pot reactions were conducted on a kilogram scale and produ
- Wagner, Jochen,Ciesielski, Michael,Fleckenstein, Christoph A.,Denecke, Hartmut,Garlichs, Florian,Ball, Andreas,Doering, Manfred
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- Regio- and stereoselective hydrothiolation reactions of ynamides with diphenyldithiophosphinic acid: Straightforward synthesis of ketene N,S-acetal derivatives
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Treatment of N-1-alkynyl-N-methylarenesulfonamides with diphenyldithiophosphinic acid resulted in hydrothiolation reactions to provide ketene N,S-acetal derivatives regio- and stereoselectively. Copyright
- Yasui, Hiroto,Yorimitsu, Hideki,Oshima, Koichiro
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- Regio- and stereoselective additions of diphenyldithiophosphinic acid to N-(1-alkynyl)amides and 1-alkynyl sulfides
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Treatment of N-(l-alkynyl)amides and 1-alkynyl sulfides with diphenyldithiophosphinic acid affords (E)-ketene N,S-acetals and S.S-acetals, respectively. The addition reactions proceed in syn fashions, which consist of protonation of the electron-rich alkynes and the following nucleophilic addition of diphenyldithiophosphinate anion to the resulting cationic intermediates.
- Kanemura, Shigenari,Kondoh, Azusa,Yasui, Hiroto,Yorimitsu, Hideki,Oshima, Koichiro
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experimental part
p. 506 - 514
(2009/04/07)
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- (Salen)Ti(IV) complex catalyzed asymmetric ring-opening of epoxides using dithiophosphorus acid as the nucleophile
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A series of chiral bis-Schiff bases were synthesized starting from (1R,2R)-(+)-diaminocyclohexane, (+)-cis-1,2,2-trimethyl-1,3-diaminocyclopentane, (R)-2,2′-diamino-1,1′-binaphthalene, and (1S,2S)-diphenyl-1,2-ethanediamine. The enantioselective ring-opening of meso epoxides with dithiophosphorus acids catalyzed by a (salen)Ti(IV) complex formed in situ upon the treatment of Ti(OPr-i)4 and the aforementioned chiral Schiff base was realized. The resulting products were obtained with low to good enantioselectivities (up to 73% ee). The (salen)Ti(IV) complex containing the backbone of 1,2-diaminocyclohexane exhibited the best enantioselectivity. The substituents in dithiophosphorus acids and those on the salen aromatic ring have a significant influence on the reaction. Moderate enantioselectivity were obtained for the (salen)Ti(IV) complex catalyzed ring-opening of racemic monosubstituted epoxides. High regioselectivity was observed for the alkyl substituted epoxides, whereas poor regioselectivity was obtained for the aryl substituted ones.
- Zhou, Zhenghong,Li, Zhaoming,Quanyong, Wang,Liu, Bing,Li, Kangying,Zhao, Guofeng,Zhou, Qilin,Tang, Chuchi
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p. 5802 - 5809
(2007/10/03)
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- Synthesis of S-thioacyl dithiophosphates, efficient and chemoselective thioacylating agents
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Easily available acyl dithiophosphates are not stable and isomerise reversibly to O-thioacyl monothiophosphates, especially when subjected to heating. Much slower but probably irreversible isomerisation to S-thioacyl monothiophosphates occurs. Since equilibrium states are established and S-thioacyl (mono)thiophosphates form slowly, reaction mixtures contain generally both thioacylating and acylating agents, and consequently cannot be used for efficient thioacylation. On the other hand, treatment of a mixture of isomeric anhydrides with an excess of a dithiophosphoric acid leads to exclusive formation of S-thioacyl dithiophosphates. They appear to be excellent thioacylating agents: relatively stable, inert towards water and oxygen and therefore easy to handle. Reactions with nitrogen or sulfur nucleophiles proceed very rapidly under ambient conditions, yielding respective thioacyl derivatives. Isolation of the products is very simple. Due to the low reactivity of S-thioacyl dithiophosphates towards oxygen nucleophiles they can be used for direct thioacylation of multifunctional nucleophiles with unprotected hydroxy groups. Respective thioacyl derivatives cannot readily be obtained using other methods.
- Doszczak, Leszek,Rachon, Janusz
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p. 1271 - 1279
(2007/10/03)
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