Cyclopenta-1,3-diene;5-ethenylcyclopenta-1,3-diene;iron(2+) → Tris(trichlorosilyl)silylvinylferrocene

HRID 2038540

Reaction equation

HRID 2038540 reaction equation
[Cl:1][Si:2]([SiH:5]([Si:10]([Cl:13])([Cl:12])[Cl:11])[Si:6]([Cl:9])([Cl:8])[Cl:7])([Cl:4])[Cl:3].[CH:14]([C-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1)=[CH2:15].[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Cl:11][Si:10]([Si:5]([CH:15]=[CH:14][C-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1)([Si:6]([Cl:9])([Cl:8])[Cl:7])[Si:2]([Cl:1])([Cl:3])[Cl:4])([Cl:13])[Cl:12].[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26]

Participants

5

Reactant 2

HCID 15807218Cyclopenta-1,3-diene;5-ethenylcyclopenta-1,3-diene;iron(2+)HCID 71388227Trisilane, 1,1,1,3,3,3-hexachloro-2-(trichlorosilyl)-

Product 1

HCID 131731029Tris(trichlorosilyl)silylvinylferrocene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 84599Chlorotris(triphenylphosphine)rhodium(I)Solvent

Procedure

Tris(trichlorosilyl)silane prepared in Example 9 is dissolved in toluene with a molar equivalent of vinylferrocene and tris(triphenylphoshine)rhodium chloride (Wilkinson's catalyst) and heated for >4 hours to form tris(trichlorosilyl)silylvinylferrocene by dehydrogenative coupling. This intermediate can be reduced to form 2-(2-ferrocenylethenyl)isotetrasilane (formula (15)), as described in Example 3.

Workup

  1. temperatureheated for >4 hours

Sources & evidence

ORD record
ord-d8de40ac4c474f0a9b81990883ce4636
Source dataset
uspto-grants-2013_11
Patent number
US08575381B2

Linked notes

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