Chloride → N~9~,N~10~-Bis(trimethylsilyl)phenanthrene-9,10-diimine

HRID 1196113

Reaction equation

HRID 1196113 reaction equation
[CH:1]1[C:14]2[C:13](=O)[C:12](=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C[Si]([N-:21][Si:22]([CH3:25])([CH3:24])[CH3:23])(C)C.[Na+].C1(=O)C2C=CC3C(=CC=CC=3)C=2C=CC1=O.C1(=N)C2C=CC3C(=CC=CC=3)C=2C=CC1=N.[Cl-]>>[CH3:23][Si:22]([N:21]=[C:13]1[C:12](=[N:21][Si:22]([CH3:23])([CH3:24])[CH3:25])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:14]1=[CH:1][CH:2]=[CH:3][CH:4]=2)([CH3:25])[CH3:24]

Participants

6

Reactant 5

HCID 312ChlorideHCID 67639,10-PhenanthrenedioneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 30805661,2-PhenanthrenedioneHCID 86745785Phenanthrenequinone diimine

Product 1

HCID 71349758N~9~,N~10~-Bis(trimethylsilyl)phenanthrene-9,10-diimineYield 37%

Procedure

Ligand Synthesis. 9,10-Phenanthrenequinone bis((trimethylsilyl)-imine) (silylphi) was synthesized from 9,10-phenanthrenequinone (Aldrich) and sodium bis(trimethylsilyl)amide (Fluka) as described by Tuchtenhagan and Ruhlmann. (11) Important modifications to this synthesis include a reaction temperature of no greater than 65° C. and a final phenanthrenequinone concentration of 0.08 M. Under these conditions, orange crystalline silylphi was obtained in 37% yield and stored under nitrogen. The phenanthrenequinone diimine ligand (phi) was generated and chelated in situ by combining the silylated imine ligand with an ethanolic solution of metal chloride by using a modificaiton of Schlosser's method. (12)

Workup

  1. customLigand Synthesis
  2. customa reaction temperature of no greater than 65° C.
  3. customUnder these conditions, orange crystalline silylphi was obtained in 37% yield

Sources & evidence

ORD record
ord-0f445a9289244094b55915f4cb38ef55
Source dataset
uspto-grants-1992_05
Patent number
US05112974

Linked notes

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