Unsymmetrical Tertiary Phosphines of Ferrocene by Friedel-Crafts Reactions. I. Ferrocenylphenylphosphines

Sollott, Gilbert P.; Mertwoy, H.; Portnoy, Seymour; Snead, Jonathan L.

doi:10.1021/jo01039a055

Cited by 91 publications

(50 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Other solvents were bubbled with nitrogen for at least 20 minutes before use. Pd(dba) 2 , [19] Pd 2 (dba) 3 , [20] P(Fc) 3 , [21] P(Fc) 2 Ph, [22] P(Fc)Ph 2 , [22] PPh 2 H, [23] P(2-Fu) 3 , [24] P(2-Fu)Ph 2 [25] and Pt(dba) 2 [26] were prepared according to literature methods. C 60 (99.9%) is available commercially.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization and Properties of Transition Metal Pd/Pt [60]Fullerene Complexes Containing Phosphane Ligands − Crystal Structure of [Pd(η²‐C₆₀){Ph₂PCH₂(CH₂OCH₂)₂CH₂PPh₂}]

Song

Wang

et al. 2004

Eur J Inorg Chem

View full text Add to dashboard Cite

A solution of C 60 in toluene reacts with Pd(dba) 2 or Pd 2 (dba) 3 (dba = dibenzylideneacetone) and monophosphanes in a 1:1:2 molar ratio to give the corresponding Pd monophos-Ph 5], whereas reaction with M(dba) 2 (M = Pd, Pt) and subsequent treatment with diphosphanes in 1:1:1 molar ratio afforded the corresponding Pd/Pt diphosphane fullerene complexes [Pd(η 2 -C 60 ){Ph 2 PCH 2 (CH 2 -OCH 2 ) n CH 2 PPh 2 }] (n = 1 6; n = 2 7; n = 3 8) and [Pt(η 2 -C 60 )-

show abstract

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization and Properties of Transition Metal Pd/Pt [60]Fullerene Complexes Containing Phosphane Ligands − Crystal Structure of [Pd(η²‐C₆₀){Ph₂PCH₂(CH₂OCH₂)₂CH₂PPh₂}]

Song

Wang

et al. 2004

Eur J Inorg Chem

View full text Add to dashboard Cite

show abstract

“…Reaction ofPFcPhz with Fe-,(CO)lz. Ferrocenyldiphenylphosphine (29)(30) (c) The reagents were dissolved in hexanes (10 mL) and irradiated for 60 min. Chromatographic work-up afforded Fe3(CO) '(PPh2Fc) in -40% yield.…”

Section: Methodsmentioning

confidence: 99%

Some reactions of ferrocenyl phosphines with M₃(CO)₁₂ (M = Fe, Ru). The structures of Ru₃(CO)₁₁(PFcPh₂) and Ru₃(CO)₁₀{(PPh₂-η-C₅H₄)₂Fe}

Chacon¹,

Cullen²,

Bruce³

et al. 1990

Can. J. Chem.

View full text Add to dashboard Cite

Tertiary phosphine substituted metal carbonyl complexes are generally very well known (1) although there have been only a few studies in this area involving ferrocenylphosphines such as PFc,Ph,-,, n = 1-3 (2-8) (FcH = Fe(q-CSH5)2), and 1,l'-disubstituted ferrocene derivatives such as dppf, l,lf-bis(dipheny1phosphino)ferrocene (2,9,10). Phosphine derivatives are generally prepared by direct reaction of the phosphine with the metal carbonyl. Sometimes, and especially in the case of Fe3(C0)12, cluster breakdown is found so that the isolated products are phosphine derivatives of mononuclear carbonyls, e.g. (Fe(C0)4(PR3) and Fe(C0)3(PR3)2 (3,5, 8, 1 1 -16). Reactions of this type involving R u~( C O )~~ usually afford trinuclear products (17)(18)(19)(20). Photosubstitution of R u~( C O )~~ seems to occur largely from higher energy states whereas photofragmentation involves the lowest excited state (20). The use of the radical anion, sodium diphenylketyl, as a catalyst has recently greatly facilitated the preparation of a wide range of derivatives Ru3(CO),,-,L,, n = 1-4, because the reactions are essentially stoichiometric (21). The method is also useful for the synthesis of derivatives of Fe3(C0)12. Salts of the bis(tripheny1phos-phine)iminium ion, ppn+, are also effective catalysts (22).In view of the success in trapping a benzyne fragment on a metal cluster from reactions of arylphosphines with M3(CO),2 'Author to whom correspondence may be addressed.(M = Ru, 0 s ) (23-25) directly or stepwise, we have initiated a study of the corresponding reactions of ferrocenylphosphines in the hope that this will lead to the trapping of a ferrocyne fragment. The present paper describes the synthesis of some derivatives of Fe3(C0)12 and R U~( C O )~~, because of our interest in their pyrolysis products, and the crystal structures of R u~( C O )~ I(PF~Ph2) and Ru3(CO) ,o(p-dppf). The thermal decomposition of R U~( C O )~, , ( P F C P~~)~ to a benzyne complex has been reported (25). Experimental sectionReactions were carried out in a nitrogen atmosphere by using standard Schlenk procedures. Solvents were dried and distilled before use. Separation of products was usually achieved by column chromatography on Florisil or neutral alumina (activity I) by using petroleum ether (35-60°C bp fraction)/diethyl ether mixtures as eluent. I H NMR spectra were recorded from CDC13 solutions by using Bruker WH400 or WP80 and Varian XL300 instruments. Infrared spectra, usually of C6H12 solutions, were run on a Bowman Fourier Transform or a Perkin Elmer 589 spectrometer. Mass spectra were obtained from a Kratos MS 50 instrument; only peaks with high m / e values are listed and electron impact ionization was used unless otherwise stated. Elemental analyses were determined by Mr. P. Borda of the Chemistry Department, University of British Columbia. Melting points were measured by using a Kofler microheating stage and are uncorrected. A Hanovia lOOW lamp (903A-1) was used for UV irradiations. To minimize

show abstract

“…Ni(CO) 4 was purchased from Aldrich and used as received. FcPPh 2 , [82] fc(PPh 2 ) 2 , [83] and fc(P(p-tolyl) 2 ) 2 [83] were prepared according to published procedures. Infrared spectra were recorded with a Perkin Elmer FT-IR spectrometer Spectrum 1000.…”

Section: General Remarksmentioning

confidence: 99%

Ferrocenyl phosphane nickel carbonyls: Synthesis, solid state structure, and their use as catalysts in the oligomerization of ethylene

Schaarschmidt

Kühnert

Tripke

et al. 2010

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

Unsymmetrical Tertiary Phosphines of Ferrocene by Friedel-Crafts Reactions. I. Ferrocenylphenylphosphines

Cited by 91 publications

References 0 publications

Synthesis, Characterization and Properties of Transition Metal Pd/Pt [60]Fullerene Complexes Containing Phosphane Ligands − Crystal Structure of [Pd(η²‐C₆₀){Ph₂PCH₂(CH₂OCH₂)₂CH₂PPh₂}]

Synthesis, Characterization and Properties of Transition Metal Pd/Pt [60]Fullerene Complexes Containing Phosphane Ligands − Crystal Structure of [Pd(η²‐C₆₀){Ph₂PCH₂(CH₂OCH₂)₂CH₂PPh₂}]

Some reactions of ferrocenyl phosphines with M₃(CO)₁₂ (M = Fe, Ru). The structures of Ru₃(CO)₁₁(PFcPh₂) and Ru₃(CO)₁₀{(PPh₂-η-C₅H₄)₂Fe}

Ferrocenyl phosphane nickel carbonyls: Synthesis, solid state structure, and their use as catalysts in the oligomerization of ethylene

Contact Info

Product

Resources

About

Unsymmetrical Tertiary Phosphines of Ferrocene by Friedel-Crafts Reactions. I. Ferrocenylphenylphosphines

Cited by 91 publications

References 0 publications

Synthesis, Characterization and Properties of Transition Metal Pd/Pt [60]Fullerene Complexes Containing Phosphane Ligands − Crystal Structure of [Pd(η2‐C60){Ph2PCH2(CH2OCH2)2CH2PPh2}]

Synthesis, Characterization and Properties of Transition Metal Pd/Pt [60]Fullerene Complexes Containing Phosphane Ligands − Crystal Structure of [Pd(η2‐C60){Ph2PCH2(CH2OCH2)2CH2PPh2}]

Some reactions of ferrocenyl phosphines with M3(CO)12 (M = Fe, Ru). The structures of Ru3(CO)11(PFcPh2) and Ru3(CO)10{(PPh2-η-C5H4)2Fe}

Ferrocenyl phosphane nickel carbonyls: Synthesis, solid state structure, and their use as catalysts in the oligomerization of ethylene

Contact Info

Product

Resources

About

Synthesis, Characterization and Properties of Transition Metal Pd/Pt [60]Fullerene Complexes Containing Phosphane Ligands − Crystal Structure of [Pd(η²‐C₆₀){Ph₂PCH₂(CH₂OCH₂)₂CH₂PPh₂}]

Synthesis, Characterization and Properties of Transition Metal Pd/Pt [60]Fullerene Complexes Containing Phosphane Ligands − Crystal Structure of [Pd(η²‐C₆₀){Ph₂PCH₂(CH₂OCH₂)₂CH₂PPh₂}]

Some reactions of ferrocenyl phosphines with M₃(CO)₁₂ (M = Fe, Ru). The structures of Ru₃(CO)₁₁(PFcPh₂) and Ru₃(CO)₁₀{(PPh₂-η-C₅H₄)₂Fe}