1,​3-​Hexadiene → HCID 22717334, compound

HRID 1583089Notes

Reaction equation

HRID 1583089 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH:4][CH2:5][CH3:6].[Cl:7][SiH:8]([Cl:10])[Cl:9]>[Cl-].C([P+](CCCC)(CCCC)CCCC)CCC>[CH3:1][CH:2]1[Si:8]([Cl:9])([Cl:7])[CH:5]([CH3:6])[CH:4]=[CH:3]1.[Cl:7][Si:8]([Cl:10])([Cl:9])[CH:2]([CH:3]=[CH:4][CH:5]([Si:8]([Cl:10])([Cl:9])[Cl:7])[CH3:6])[CH3:1]

Participants

5

Reactant 2

HCID 116021,​3-​HexadieneHCID 24811Trichlorosilane

Product 2

HCID 22717334HCID 22717334, compoundYield 74%HCID 73993291HCID 73993291, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 75311Tetrabutylphosphonium chlorideCatalyst

Conditions

Temperature
180 °C

Procedure

As in Example 1, 1,3-hexadiene (1.00 g, 12.17 mmol), trichlorosilane (6.59 g, 48.65 mmol) and tetrabutylphosphonium chloride (0.36 g, 1.22 mmol) were added in a 25 mL stainless steel tube under nitrogen atmosphere. After sealing the cylinder with a cap, the reactor was maintained at 180° C. for 8 hours. The resulting mixture was distilled to yield 1.64 g (yield: 74%) of 1,1-dichloro-2,5-dimethylsilacyclo-3-pentene and 0.43 g (yield: 10%) of 2,5-bis(trichlorosilyl)-3-hexene main products.

Workup

  1. distillationThe resulting mixture was distilled

Sources & evidence

ORD record
ord-2d35793a6a124ce39e9777bf5c570979
Source dataset
uspto-grants-2004_05
Patent number
US06740766B2

Reaction notes

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