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inquirymethanol
methylenebis(diphenylphosphane)-borane(1:2)
A
Trimethyl borate
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In toluene at 100℃; Inert atmosphere; | A n/a B 100% |
Conditions | Yield |
---|---|
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 16h; | 95% |
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 16h; | 95% |
Stage #1: diphenylphosphane With cesiumhydroxide monohydrate In N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve; Inert atmosphere; Stage #2: 1,2-dibromomethane In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; Molecular sieve; | 95% |
ethanol
methylenebis(diphenylphosphane)-borane(1:2)
A
triethyl borate
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Inert atmosphere; Reflux; | A n/a B 91% |
Conditions | Yield |
---|---|
Stage #1: tetraphenyldiphosphine oxide; Cp2Ti=CH2 In benzene at 50℃; Stage #2: at 80℃; | 66% |
Conditions | Yield |
---|---|
With tris(dimethylamino)(methylimino)phosphorane In tetrahydrofuran; diethyl ether for 24h; Ambient temperature; | 50% |
With potassium hydroxide; potassium carbonate 1.) HMPT, 20 deg C, 2.) 40 - 45 deg C, 1 h; Yield given. Multistep reaction; | |
With potassium hydroxide; potassium carbonate 1) HMPA, 20 deg C, 2) HMPA, 40-45 deg C, 1 h; Yield given. Multistep reaction; |
chloroform
potassium diphenylphosphine
A
Tetraphenyldiphosphin
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In ammonia at -50℃; | A n/a B 45% |
In ammonia at -50℃; Product distribution; Mechanism; another solvent; | A n/a B 45% |
Conditions | Yield |
---|---|
With sodium und Umsetzung mit CH2Cl2; |
(diphenylphosphinomethyl)diphenylphosphine sulphide
A
bis(diphenylthiophosphoryl)methane
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
at 150℃; vacuum; | |
at 150℃; vacuum sublimation; |
Lithium-bis(diphenylphosphanyl)methanid
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.25h; Ambient temperature; |
C25H21CsP2
cyclohexylamine
A
Caesium-cyclohexylamid
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Equilibrium constant; pK; |
Conditions | Yield |
---|---|
With Pd2(bis(diphenylphosphino)methane)3 Quantum yield; Irradiation; |
Conditions | Yield |
---|---|
With phosphazene base-P4-tert-butyl In tetrahydrofuran; diethyl ether for 24h; Ambient temperature; Yield given; |
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at 0℃; for 0.5h; |
PdPtCoI(CO)3(dppm)2
A
{Pd(η2-dppm)(DMSO)2}I2
B
{Pt(η2-dppm)(DMSO)2}I2
C
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With iodine In dimethyl sulfoxide To a soln. of PdPtCoI(CO)3(dppm)2 in DMSO was added I2. This resulted in an immediate color change from deep red to red-orange.; Not isolated. Detected by (31)P-NMR.; |
A
Co2(CO)4(μ-CO)2(μ-bis(diphenylphosphino)methane)
C
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With CO In not given in presence of CO; not isolated; detected by NMR; |
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In not given equilibrium in soln.; (31)P NMR data; |
Pt((C6H5)2PCH2P(C6H5)2)2(C6F5)2
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In not given equilibrium in soln.; (31)P NMR data; |
A
(μ2-CH2)(Cl)2(bis(diphenylphosphino)methane)2dipalladium
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With dichloromethane In dichloromethane Irradiation (UV/VIS); |
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In dichloromethane warming the soln. to ambient temp.; |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Zn / acetonitrile 2: CO / not given View Scheme |
Co2(CO)4(μ-CO)2(μ-bis(diphenylphosphino)methane)
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: I2 / tetrahydrofuran 2: Zn / acetonitrile 3: CO / not given View Scheme |
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: not given 2: not given View Scheme |
diphenyl(trimethylsilylmethyl)phosphane
A
bis[{(trimethylsilyl)methyl}phenylphosphino]methane
B
<(Diphenylarsino)methyl>diphenylphosphan
E
Diphenylphosphine oxide
F
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With arsenic trichloride In neat (no solvent) at 90 - 100℃; Solvent; |
dichlorophenylarsine
diphenyl(trimethylsilylmethyl)phosphane
A
dpma
B
<(Diphenylarsino)methyl>diphenylphosphan
C
bis(diphenylphosphino)methane monooxide
E
diphenyl(methyl)phosphine
F
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In neat (no solvent) at 90 - 100℃; Inert atmosphere; |
mer,cis-(Mn(CO)2(dppm-PP')(dppm-P)Br)
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With sodium methylate In methanol for 72h; Guerbet Reaction; Glovebox; |
Conditions | Yield |
---|---|
With HOF* CH3CN In dichloromethane at 0℃; for 0.0833333h; | 100% |
With dihydrogen peroxide In dichloromethane; water for 0.0833333h; | 93% |
With dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 2h; | 90% |
{(carbonyl)3cobalt(μ-hexafluorobut-2-yne)cobalt(carbonyl)3}
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With benzophenone ketyl In not given inert gas; 293 K; a small amount benzophenone ketyl was added to a solution of the metal complex and the P-compound; solvent was removed; chromatographed; | 100% |
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
bis-diphenylphosphinomethane
A
tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0)
B
bicyclo[2.2.1]hepta-2,5-diene
Conditions | Yield |
---|---|
In tetrahydrofuran reaction in a calorimeter under argon; | A 100% B n/a |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In toluene (N2 or Ar); complex added to ligand soln., suspn. stirred at 80°C for 15 h; filtered off, washed with toluene and Et2O; | 100% |
In toluene at 80℃; for 12h; |
trichlorotris(tetrahydrofuran)molybdenum(III)
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Mo(III) complex and excess diphosphine heating to melting point of the diphosphine for 10 min, on cooling the solid washing with hot toluene; identified by elem. anal., and IR spectrum; | 100% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In acetone PtCl2 was reacted with ligand in boiling acetone for 5 h; | 100% |
pentacarbonyl-(μ-di-tert-butylphosphido)-(μ-dicyclohexylphosphido)diiron
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In tetrahydrofuran (Ar); stirring (25°C, 2 h); solvent removal (vac.), extracting (pentane), filtn., solvent redn. (vac.), crystn. (-30°C); elem. anal.; | 100% |
Conditions | Yield |
---|---|
for 0.0833333h; Sonication; | A 100% B n/a |
trichlorotris(tetrahydrofuran)chromium(III)
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In not given ligand reacted with Cr complex (A.Bollmann, K.Blann, J.T.Dixon, F.M.Hess, E.Killian et al. J. Am. Chem. Soc. 126 (2004) 14712); elem. anal.; | 99% |
[(PPh3)ClPd(μ-[C=C(H)-N=CPh2])PdCl(PPh3)2]*toluene
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In dichloromethane byproducts: PPh3; all manipulations under purified N2; org. compd. added to soln. of Pd complex, stirred for 10 min; solvent removed in vac., residue rinsed with Et2O, dried, elem. anal.; | 99% |
[MoCl(SnCl3)(CO)3(NCCH3)2]
bis-diphenylphosphinomethane
MoCl(SnCl3)(CO)3((C6H5)2P(CH2)P(C6H5)2)
Conditions | Yield |
---|---|
In acetone stirring 30 min, under dry nitrogen stream; removal of solvent in vacuo, elem anal.; | 99% |
cis-dirhenium diacetate tetrachloride dihydrate
bis-diphenylphosphinomethane
[Re2Cl4(μ-bis(diphenylphosphino)methane)2]
Conditions | Yield |
---|---|
In ethanol by refluxing ethanol soln. contg. cis-Re2(μ-O2CCH3)2Cl4(H2O)2 and bis(diphenylphosphino)methane for 18 h under N2; | 99% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In dichloromethane byproducts: cyclooctadiene; under Ar; to a soln. of the Pt complex and the phosphine in CH2Cl2 was added NH4PF6, stirred for 3 h; solvent was removed, washed with pentane, redissolved in CH2Cl2, passed through an alumina column, evapd. to dryness, washed with pentane, dried in vac.; elem. anal.; | 99% |
[Mo2(η5-cyclopentadienyl)2(μ-H)(μ-PCy2)(CO)2]
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In toluene (N2); stirring molybdenum compd. and phosphine deriv. in toluene at roomtemp. for 2 h; | 99% |
1,4-pyrazine
methanol
bis-diphenylphosphinomethane
copper(I) bromide
Conditions | Yield |
---|---|
In dichloromethane mixt. of CuBr, C4H4N2 and (Ph2P)2CH2 (1:2:1 molar ratio) in CH2Cl2 stirred (6 h, ambient temp.); elem. anal.; | 99% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
heating; | 99% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
heating; | 99% |
silver trifluoromethanesulfonate
mercuric triflate
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In dichloromethane | 99% |
Conditions | Yield |
---|---|
With Et3N In acetonitrile byproducts: [Et3NH]NO3; alcohol-comp. then excess of Et3N were added to 3 equiv. of AgNO3 in MeCN, stirring for 3 h, 3 equiv. of solid P-compd. was added, stirring for 18 h; soln. was filtered through Celite, evapd. to dryness, solid was washed with H2O, Et2O and dried, recrystn. from CH2Cl2/hexane; | 99% |
2,4,6-trimethylbenzylbromide
bis-diphenylphosphinomethane
[(diphenylphosphino)methyl]diphenyl[(2,4,6-trimethylphenyl)methyl]phosphonium bromide
Conditions | Yield |
---|---|
In toluene at 80℃; for 48h; Inert atmosphere; | 99% |
bis-diphenylphosphinomethane
(diphenylphosphinomethyl)(ferrocenylmethyl)diphenylphosphoniumiodide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide byproducts: N(CH3)3; (N2), mixture stirred for 5 hat 120°C, cooled to 20°C; solvent removed in vacuo, residue washed with toluene and pentane, dried in vacuo; | 98.5% |
p-methylazidobenzene
bis-diphenylphosphinomethane
bis(N-p-tolyliminodiphenylphosphoranyl)methane
Conditions | Yield |
---|---|
In benzene at 60℃; for 4h; | 98% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With bromine In dichloromethane | 98% |
With bromine In dichloromethane at -78 - 20℃; | 100 % Spectr. |
dodecacarbonyl-triangulo-triruthenium
bis-diphenylphosphinomethane
(Ru3(CO)11)2((C6H5)2PCH2P(C6H5)2)
Conditions | Yield |
---|---|
With sodium diphenylketyl In tetrahydrofuran a THF soln. of Ph2CONa was added dropwise under N2 to a soln. of Ru3(CO)12 and dppm in 2:1 molar ratio in THF, reaction was monitored by IR spectroscopy; THF was pumped off under vac., residue recrystd.; elem. anal.; | 98% |
Conditions | Yield |
---|---|
In acetonitrile stoich. mixt. in CH3CN stirred for 12 h at room temp.; evapd., washed (Et2O), elem. anal.; | 98% |
potassium tetrachloroplatinate(II)
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With NaBH4 In acetonitrile (N2); stirring (12 h); filtn., washing (pentane), drying; | 98% |
bis-diphenylphosphinomethane
Co4(CO)7(H2C(P(C6H5)2)2)(HC(P(C6H5)2)3)
Conditions | Yield |
---|---|
In tetrahydrofuran refluxed in THF for 2 h; filtered through silica gel, evapd. to dryness; washed with diethylether; | 98% |
silver(I) hexafluorophosphate
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With n-hexane In dichloromethane; acetone ligand was added to soln. of Rh-complewx in dichloromethane, followed by soln. of AgPF6 in acetone, soln. stirred for 5 min; Et2O added, soln. filtered, filtrate evapd. to dryness under reduced pressure, residue triturated with Et2O, filtered off, washed with Et2O anddried in vacuo over P2O5, product recrystd. from acetone-n-hexane; elem. anal.; | 98% |
carbonylchlorohydridotris(triphenylphosphine)ruthenium(II)
bis-diphenylphosphinomethane
[RuHCl(CO)(PPh3)2(dppm)]
Conditions | Yield |
---|---|
In toluene in an oxygen-free environment; a suspn. of the Ru complex in toluene was treated with the phosphine, refluxed for 30 min; cooled to room temp., concd. in vac., slow addn. of pentane, filtered, washed with pentane and Et2O, dried in vac. (mixt. of cis- and trans-isomers); elem. anal.; | 98% |
In dichloromethane under N2 or Ar; addn. of phosphine to a CH2Cl2 soln. of the Ru complex,mixt. stirred (23°C, 72 h); mixt. cooled (-15°C), crystals filtered off, washed (Et2O); the mixt. of isomers could not be sepd.; | 70% |
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