Nitrogen → Bis(eta-cyclopentadienyl) iron

HRID 1823700Notes

Reaction equation

HRID 1823700 reaction equation
ClC([C-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)=O.[C-:9]1(C(Cl)=O)[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:17].C(O)CCCCCO.N#N.[Cl-].[NH+]1C=CC=CC=1>C1C=CC=CC=1.N1C=CC=CC=1>[CH-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1.[CH-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:17]

Participants

7

Reactant 4

HCID 947NitrogenHCID 123741,6-HexanediolHCID 69401Einecs 211-027-4HCID 178521104HCID 178521104, compound2×

Product 1

HCID 7611Bis(eta-cyclopentadienyl) ironYield 88%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1049PyridineSolvent

Procedure

A scheme for the synthesis of 1,1′-di(chlorocarbonyl) ferrocene is shown in FIG. 7. To the solution of 4.0 g (0.013 mole) 1,1′-di(chlorocarbonyl) ferrocene in dry benzene (95 ml), 1.82 g (0.0154 mole) 1,6-hexanediol and pyridine (1.1 ml) was added. The mixture was stirred at 70–75° C. under an inert atmosphere (N2 gas) for 4 hours. The pyridinium chloride salt, being insoluble in benzene was precipitated from the reaction phase. The mixture was filtered and the solvent was evaporated under reduced pressure. The residue was extracted with CH2Cl2 and washed with water. The organic layer was dried (Na2SO4) and evaporated to give 4.3 g (88%) of ferrocene containing hydroxyl terminated prepolymer, FcOH. 1H NMR of this compound showed an average molecular weight of −3600. 1H NMR δ: 4.83 (s, 4H), 4.40 (s, 4H), 4.24 (t, 4H), 3.68 (t, 0.43H), 1.78 (m, 4H), 1.52 (m, 4H). IR (cm−1, neat): 1722.9 (C═O), 2940.4 (CH aliphatic), 3486.7 (OH). The 1H NMR spectra were obtained with a BRUKER AMX-360 NMR spectrometer (Bruker, Billerica, Mass.) in CDCl3. The IR spectra were recorded on a NICOLET system 550 (Magna series) FTIR spectrometer (Thermo Nicolet, Madison, Wis.). A scheme for the synthesis of the ferrocene-containing hydroxyl terminated (FCOH) prepolymer is shown in FIG. 8.

Workup

  1. customwas precipitated from the reaction phase
  2. filtrationThe mixture was filtered
  3. customthe solvent was evaporated under reduced pressure
  4. extractionThe residue was extracted with CH2Cl2
  5. washwashed with water
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-99edc2d32b644ed79174ec26081c42d5
Source dataset
uspto-grants-2006_05
Patent number
US07041374B1

Reaction notes

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