2240-47-3

Usage

Uses

Used in Coordination Chemistry:
Imidotriphenylphosphorus serves as a ligand, forming stable metal complexes that are essential in various chemical reactions and processes. Its strong electron-donating nature enhances the stability and reactivity of these complexes.
Used in Catalysis:
Imidotriphenylphosphorus is utilized as a catalyst or a component of catalytic systems, facilitating various organic reactions. Its electron-donating ability makes it a valuable asset in promoting reaction rates and selectivity.
Used in the Synthesis of Organic Compounds:
imidotriphenylphosphorus is employed in the synthesis of a wide range of organic compounds, contributing to the formation of desired products with improved efficiency and yield.
Used in Pharmaceutical and Agrochemical Production:
Imidotriphenylphosphorus plays a role in the production of pharmaceuticals and agrochemicals, where its ability to form stable complexes and act as a stabilizing agent is crucial for the development of effective and stable products.
Used in Optical and Electronic Materials:
Due to its unique electronic properties, imidotriphenylphosphorus has been studied for potential applications in the development of optical and electronic materials, where its structural and electronic characteristics can contribute to the performance of these advanced materials.

InChI:InChI=1/C18H16NP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H

Upstream product

• 15729-44-9 amino(triphenyl)phosphonium chloride 
• 74255-76-8 (triphenylphosphoranylidene)ammonium azide 
• 603-35-0 triphenylphosphine 
• 916599-59-2 α-azidophenylacetonitrile 
• 67-56-1 methanol 
• 38011-30-2 bis(triphenyl-λ⁵-phosphanylidene)ammonium fluoride 
• 21050-13-5 bis(triphenylphosphine)iminium chloride 
• 15318-33-9 trans-carbonyl(chloro)bis(triphenylphosphine)rhodium(I) 
• 791-28-6 Triphenylphosphine oxide 
• 15931-69-8 bromure de triphenyl aminophosphonium 
• 13989-64-5 triphenylphosphine-N-tertbutylimine 

Downstream Products

• 74255-77-9 thiocyanic salt of P,P,P-triphenylphosphine imide 
• 13892-06-3 N-trimethylsilyl(triphenylphosphoranylidene)amine 
• 79430-41-4 N'-(phenylsulfonyl)-N-(triphenylphosphoranylidene)phosphoramidimidic dichloride 
• 19085-97-3 N-(dichlorophosphinyl)-P,P,P-triphenylphosphine imide 
• 59285-66-4 iodure de triphenyl N,N-dimethylaminophosphonium 
• 169137-94-4 (Z)-2-((R)-Toluene-4-sulfinyl)-1-trifluoromethyl-vinylamine 
• 169137-95-5 (Z)-1-(Chloro-difluoro-methyl)-2-((R)-toluene-4-sulfinyl)-vinylamine 
• 21655-90-3 N-Triphenylphosphoranyliden-benzolsulfinsaeureamid 
• 21502-37-4 N-Triphenylphosphoranyliden-4-chlor-benzolsulfinsaeureamid 
• 21655-92-5 N-Triphenylphosphoranyliden-2-nitro-benzolsulfinsaeureamid 
• 21655-94-7 N-Triphenylphosphoranyliden-4-nitro-benzolsulfinsaeureamid 

Relevant academic research and scientific papers

A facile approach to N-unsubstituted phosphinimines

Phosphine oxides (R3P = O) are conveniently converted into phosphinimines (R3P = NH) by recycling several times through the sequence: triflic anhydride; ammonia; evaporation. Half of the triflic anhydride is used at each repeat.

Low temperature neutron and X-ray diffraction study of imino(triphenyl)phosphorane

The structure of imino(triphenyl)phosphorane, Ph3PNH 1 has been determined by low-temperature X-ray and neutron diffraction. This dual study is the first such for an iminophosphorane. From the neutron diffraction data, the P-N bond length is 1.582(2) A and the P-N-H angle is 115.0(2)°.

Structure and Reactivity of a Manganese(VI) Nitrido Complex Bearing a Tetraamido Macrocyclic Ligand

Manganese complexes in +6 oxidation state are rare. Although a number of Mn(VI) nitrido complexes have been generated in solution via one-electron oxidation of the corresponding Mn(V) nitrido species, they are too unstable to isolate. Herein we report the isolation and the X-ray structure of a Mn(VI) nitrido complex, [MnVI(N)(TAML)]- (2), which was obtained by one-electron oxidation of [MnV(N)(TAML)]2- (1). 2 undergoes N atom transfer to PPh3 and styrenes to give Ph3P═NH and aziridines, respectively. A Hammett study for various p-substituted styrenes gives a V-shaped plot; this is rationalized by the ability of 2 to function as either an electrophile or a nucleophile. 2 also undergoes hydride transfer reactions with NADH analogues, such as 10-methyl-9,10-dihydroacridine (AcrH2) and 1-benzyl-1,4-dihydronicotinamide (BNAH). A kinetic isotope effect of 7.3 was obtained when kinetic studies were carried out with AcrH2 and AcrD2. The reaction of 2 with NADH analogues results in the formation of [MnV(N)(TAML-H+)]- (3), which was characterized by ESI/MS, IR spectroscopy, and X-ray crystallography. These results indicate that this reaction occurs via an initial "separated CPET"(separated concerted proton-electron transfer) mechanism; that is, there is a concerted transfer of 1 e- + 1 H+ from AcrH2 (or BNAH) to 2, in which the electron is transferred to the MnVI center, while the proton is transferred to a carbonyl oxygen of TAML rather than to the nitrido ligand.

Bioinspired oxidation of oximes to nitric oxide with dioxygen by a nonheme iron(II) complex

The ability of two iron(II) complexes, [(TpPh2)FeII(benzilate)] (1) and [(TpPh2)(FeII)2(NPP)3] (2) (TpPh2 = hydrotris(3,5-diphenylpyrazol-1-yl)borate, NPP-H = α-isonitrosopropiophenone), of a monoanionic facial N3 ligand in the O2-dependent oxidation of oximes is reported. The mononuclear complex 1 reacts with dioxygen to decarboxylate the iron-coordinated benzilate. The oximate-bridged dinuclear complex (2), which contains a high-spin (TpPh2)FeII unit and a low-spin iron(II)–oximate unit, activates dioxygen at the high-spin iron(II) center. Both the complexes exhibit the oxidative transformation of oximes to the corresponding carbonyl compounds with the incorporation of one oxygen atom from dioxygen. In the oxidation process, the oxime units are converted to nitric oxide (NO) or nitroxyl (HNO). The iron(II)–benzilate complex (1) reacts with oximes to afford HNO, whereas the iron(II)–oximate complex (2) generates NO. The results described here suggest that the oxidative transformation of oximes to NO/HNO follows different pathways depending upon the nature of co-ligand/reductant.

Pushing the Limits of Neutral Organic Electron Donors: A Tetra(iminophosphorano)-Substituted Bispyridinylidene

A new ground-state organic electron donor has been prepared that features four strongly π-donating iminophosphorano substituents on a bispyridinylidene skeleton. Cyclic voltammetry reveals a record redox potential of ?1.70 V vs. saturated calomel electrode (SCE) for the couple involving the neutral organic donor and its dication. This highly reducing organic compound can be isolated (44 %) or more conveniently generated in situ by a deprotonation reaction involving its readily prepared pyridinium ion precursor. This donor is able to reduce a variety of aryl halides, and, owing to its redox potential, was found to be the first organic donor to be effective in the thermally induced reductive S N bond cleavage of N,N-dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.

Bis(triphenyl-λ5-phosphanylidene)ammonium fluoride: A reactive fluoride source to access the hypervalent silicates [Me nSiF5-n]- (n = 0-3)

A new synthesis of bis(triphenyl-λ5-phosphanylidene) ammonium fluoride ((Ph3PNPPh3)F, abbreviated as (PNP)F), is described. The title compound has been fully characterized by multinuclear NMR spectroscopy, vibrational spectroscopy, elemental analysis and single crystal and powder X-ray diffraction for the first time. In the solid state (PNP)F exists as a covalent molecular compound, in which the fluoride ion is asymmetrically bonded to the two phosphorus atoms of the [PNP]+ cation. The phosphorus-fluorine bond with 181.98(13) pm is surprisingly long and the longest P-F bond in any phosphorane. (PNP)F can be assumed to be a very good source of reactive fluoride. To investigate the fluoride ion donating properties, (PNP)F was reacted with a range of different fluoromethylsilanes MenSiF4-n (n = 0-4). Reactions of (PNP)F with the fluoromethylsilanes were performed in aceto- or propionitrile and in 1,2-dimethoxyethane under inert conditions. The resulting hypervalent fluoromethylsilicates [MenSiF5-n]- (n = 0-3) were fully characterized by multinuclear NMR and vibrational spectroscopy and single crystal X-ray diffraction. From the reaction of (PNP)F with Me 4Si in acetonitrile, the starting materials were recovered unchanged. To aid the understanding of the experimental results the fluoride ion affinities (FIA) for these silanes have been calculated by DFT calculations on the PBE0/def2-TZVPP level of theory. The fluoride ion affinity in the series of MenSiF4-n (n = 0-4) decreases with the number of methyl groups and is too low for Me4Si to bind a fluoride ion under these reaction conditions.

The reaction of fullerene C60 with halogen azides

Reaction of fullerene C60 and halogen azides (IN3, BrN3) gives 1-halo-2-azidofullerenes, whose structures were proved by NMR and IR spectroscopy, MALDI-TOF mass spectrometry, and by their chemical transformations.

Reductive phosphine-mediated ligation of nitroxyl (HNO)

Nltroxyl (HNO) demonstrates a unique chemical and biological profile compared to nitric oxide (NO). Phosphorus NMR studies reveal that HNO reacts with triarylphosphines to give the corresponding phosphine oxide and aza-ylide. In the presence of a properly situated electrophilic ester, the aza-ylide undergoes a Staudinger ligation to yield an amide with the nitrogen atom being derived from HNO. These results define new HNO reactivity and provide the basis of new HNO detection methods.

New polysulfur-nitrogen heterocycles by thermolysis of 1, 3λ4δ2,2,4-benzodithiadiazines in the hydrocarbon and fluorocarbon series

In contrast to thermolysis of 1,3λ4δ2,2, 4-benzodithiadiazine (1) and its 5,6,7,8-tetrafluoro derivative 2 in dilute (10-3 M) hydrocarbon solutions, which leads to persistent 1,2,3-benzodithiazolyls in nearly quantitative

Unexpected Staudinger Reaction of α-Azidophenylacetonitrile and Triphenylphosphine: Synthesis and Crystal Structure of Aminotriphenylphosphonium Salt of Phenylmalononitrile

Staudinger reaction of α-azidophenylacetonitrile with triphenylphosphine in 1:2 molar ratio provides the triphenylphosphinazine derived from α-diazophenylacetonitrile, whereas in 2:1 molar ratio the final product is found to be the aminotriphenylphosphonium salt of phenylmalononitrile; X-ray structure analysis of this salt indicates that the anion and cation interact with one another via hydrogen bonding.