1,4-Diphenyl-1,3-butadiene → HCID 73993292, compound

HRID 1583091Notes

Reaction equation

[C:1]1([CH:7]=[CH:8][CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:17][SiH:18]([Cl:20])[Cl:19]>[Cl-].C([P+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:17][Si:18]([Cl:20])([Cl:19])[CH:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH:9]=[CH:8][CH:7]([Si:18]([Cl:20])([Cl:19])[Cl:17])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 180 °C

Procedure

As in Example 1, 1,4-diphenyl-1,3-butadiene (2.00 g, 9.70 mmol), trichlorosilane (5.25 g, 38.76 mmol), tetrabutylphosphonium chloride (0.29 g, 0.98 mmol) and 5 mL of toluene (solvent) 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. After removing the solvent and unreacted trichlorosilane and tetrachlorosilane through simple distillation, this reaction mixture was distilled under reduced pressure to separate the catalyst and the product. The product was recrystallized from 10 mL of n-hexane for 4 days to yield 1.51 g (yield: 51%) of 2,5-diphenyl-1,1-dichlorosilacyclo-3-pentene and 1.20 g (yield: 26%) of 1,4-bis(trichlorosilyl)-1,4-diphenyl-2-butene.

Workup

customAfter removing the solvent and unreacted trichlorosilane and tetrachlorosilane
distillationthrough simple distillation
distillationthis reaction mixture was distilled under reduced pressure
customto separate the catalyst
customThe product was recrystallized from 10 mL of n-hexane for 4 days

Sources & evidence

ORD record: ord-4a8bb9927edf43678f85eba0cc3a5b88
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740766B2

Reaction notes

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