103559-83-7

Basic information

• Product Name: hexaphenylcarbodiphosphorane
• Synonyms: hexaphenylcarbodiphosphorane
• CAS NO: 103559-83-7
• Molecular Weight: 536.593
• Mol File: 103559-83-7.mol

Chemical Properties

• CAS DataBase Reference: hexaphenylcarbodiphosphorane(CAS DataBase Reference)
• NIST Chemistry Reference: hexaphenylcarbodiphosphorane(103559-83-7)
• EPA Substance Registry System: hexaphenylcarbodiphosphorane(103559-83-7)

Safety Data

• Hazardous Substances Data: 103559-83-7(Hazardous Substances Data)

Upstream product

• 603-35-0 triphenylphosphine 
• 558-13-4 carbon tetrabromide 
• 56-23-5 tetrachloromethane 
• 82813-03-4 C₃₇H₃₀P₂S 
• 14529-09-0 methylenebis(triphenylphosphonium) dibromide 

Downstream Products

• 7533-53-1 O₂CC(PPh₃)2 
• 488148-43-2 [(AuCl)2(μ-C(PPh3)2)] 
• 1187741-76-9 3-[(triphenylphosphoranylidene)methylene]naphtho[2,1-b]furan-2-one 
• 791-28-6 Triphenylphosphine oxide 
• 1187741-78-1 2,5-diphenyl-4-[(triphenylphosphoranylidene)methylene]cyclohexa-2,5-diene-1-one 
• 1187741-86-1 triphenyl(3,4-dihydro-2,2,2-triphenyl-2H-1,2-oxaphosphino[5,6-h]quinolin-3-ylidene)phosphine 
• 1187741-82-7 2-[phenyl-[1,1,1-triphenyl]phosphino]hydrazono-[(triphenylphosphoranylidene)-methyl]indane-1,3-dione 
• 1187741-79-2 1,3-dioxo-2-[(triphenylphosphinio)(triphenylphosphoranylidene)methyl]indan-2-olat 
• 1187741-80-5 2-hydroxy-3-[(triphenylphosphoranylidene)methylene]-2,3-dihydroisoindol-1-one 
• 1187741-81-6 3-[(triphenylphosphoranylidene)methylene]indan-1-one 
• 1187741-83-8 6-chloro-N-(2-chloro-4-nitrophenyl)-3,4-dihydro-2,2,2-triphenyl-3-(triphenylphosphoranylidene)-2H-benzo[e]-1,2-oxaphosphin-8-carboxamide 
• 1013101-77-3 HC(P(C₆H₅)3)2⁽¹⁺⁾*Co(CO)4^(1-)=HC(P(C₆H₅)3)2Co(CO)4 
• 868602-71-5 [(η3-C8H11)Pt(C6H4PPh2CPPh3)] 
• 851591-29-2 [(C₈H₁₂)Rh(C₆H₄P(C₆H₅)2CP(C₆H₅)3)] 

Relevant articles and documents

Synthetic and NMR studies on hexaphenylcarbodiphosphorane (Ph3P[dbnd]C[dbnd]PPh3)

Bisylides of the type R3P[dbnd]C[dbnd]PR3, also known as carbodiphosphoranes, are very reactive compounds having numerous unusual and promising properties. The first representatives of this class of divalent carbon(0) compounds have already been synthesized over 50 years ago, but aspects of their chemistry and properties remain ambiguous. Herein, we report on specific characteristics of a simple carbodiphosphorane, hexaphenylcarbodiphosphorane Ph3P[dbnd]C[dbnd]PPh3, based on 1H, 13C, and 31P NMR studies. The chemical shift and 1JCP coupling characteristics of the central sp-hybridized carbon atom are compared to those of other sp-hybridized carbons. Our spectroscopic findings are supported by simulations, which are in very good agreement with the experimentally determined values.

Three and four coordinate Fe carbodiphosphorane complexes

Carbodiphosphoranes (CDPs) are a family of divalent carbon ligands that are known for their exceptional electron donor properties. Herein, the preparation and reactivity of a family of three and four co-ordinate Fe carbodiphosphorane complexes is describe

Evaluation of the electronic properties of a carbodiphosphorane through gold catalysis

Carbodiphosphoranes [C(PR3)2] are divalent carbon(0) derivatives which can be used as ligands to form either M←C(PR 3)2 or (M)2← C(PR3)2 species. They were computationally predicted to be even stronger electron donors than N-heterocyclic carbenes. We have introduced hexaphenylcarbodiphosphorane [C(PPh3)2] for the first time in gold catalysis in order to validate this prediction by experimentation. Its mono- and digold complexes were compared to tris(2,4-di-tert-butylphenyl) phosphite, triphenylphosphine, and 1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidene in representative gold(I)-catalyzed transformations. The advantages and limitations of these ligands are discussed. Copyright

Cyanophosphorus Compounds, 8. The Unusual Anion P2C10N102-

The reaction P(CN)3 + CN- (as crown-6-sodium salt) leads via the spectroscopically identified P(CN)4- to a disproportionation PIII -> PI + PV.P(CN)2- and P2C10N102- (1) have

Reactions of Hexaphenylcarbodiphosphorane, IV. Reactions of Hexaphenylcarbodiphosphorane with Halogen Compounds. Diphosphaallyl Cations

Hexaphenylcarbodiphosphorane (1) undergoes nucleophilic displacement reaction with halogen compounds 3 with formation of compounds 5 which can be regarded as salts of the diphosphaallylcation. 1 reacts with bromoacetic ester 11 as base, with proton abstraction and formation of a carbanion 12 which gives rise to formation of (E)-cyclopropantricarboxylicacid ester (13).In an analogous way, 1 attacks isothiocyanatoaceticacid ester (14) with formation of an ionpair 15 which undergoes a cycloaddition with a second molecule 14 forming 16, which can be converted into the mercaptothiazol derivative 17 by treatment with HCl. - Key words: Hexaphenylcarbodiphosphorane Diphosphaallyl Cations, 13C NMR Spectra

A NEW METHOD FOR THE PREPARATION OF (2,2-DIPHENYLVINYLIDENE)-TRIPHENYLPHOSPHORANE AND ITS REACTION WITH CARBONYL COMPOUNDS

Hexaphenylcarbodiphosphorane (I), prepared from triphenylphosphine and carbon tetrahalide, when treated with benzophenone in equimolar ratio, gave the ylide (2,2-diphenylvinylidene)triphenylphosphorane (II) which, upon further treatment with benzophenone, gave 1,3-tetraphenylallene (III) via Witting reaction.

A New Method for the Preparation of Carbodiphosphorane and Its Reaction with Carbonyl Compounds

The simple and new method for the preparation of hexaphenylcarbodiphosphorane (II) involves the reaction of triphenylphosphine and carbon tetrahalide in 4 : 1 molar ratio .Reaction of II with carbonyl compounds affords phosphoranyl 1,2-oxaphosphetanes (IV-VI).