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
• Article Data: 8

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

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

Downstream Products

• 7533-53-1 O₂CC(PPh₃)2 
• 86847-10-1 [AuCl{C(PPh₃)2}] 
• 52615-01-7 (CO)3NiC(PPh₃)2 
• 220790-97-6 (CO)2NiC(PPh₃)2 
• 1013101-77-3 HC(P(C₆H₅)3)2⁽¹⁺⁾*Co(CO)4^(1-)=HC(P(C₆H₅)3)2Co(CO)4 
• 1246535-11-4 (PPh₃)2CCPhCHB(C₆F₅)3] 
• 1246535-04-5 [(Ph₃P)2CH][HB(C₆F₅)3] 
• 110354-19-3 (η5-cyclopentadienyl){(triphenylphosphonio)(triphenylphosphoranylidene)methyl}copper(I) 
• 110354-18-2 (η5-pentamethylcyclopentadienyl){(triphenylphosphonio)(triphenylphosphoranylidene)methyl}copper(I) 
• 110354-20-6 (η5-pentamethylcyclopentadienyl){(triphenylphosphonio)(triphenylphosphoranylidene)methyl}silver(I) 
• 488148-44-3 [Au(CH₃C(O)CHC(O)CH₃)(C(P(C₆H₅)3)2)] 
• 488148-46-5 [Au(CCC₆H₅)(C(P(C₆H₅)3)2)] 
• 488148-65-8 [Au(CCC₆H₄CN-4)(C(P(C₆H₅)3)2)] 
• 488148-55-6 [Au(CCC₆H₄NO₂-4)(C(P(C₆H₅)3)2)] 

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.

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

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