Styrene → 1,1,3,3-TETRAMETHYL-1,3-DI(2-PHENYLETHYL) DISILOXANE

HRID 379283Notes

Reaction equation

HRID 379283 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[SiH](C)O[SiH](C)C.C(OC(=O)C)(=O)C.FC(F)(F)S(O[Si](C(C)C)(C(C)C)C(C)C)(=O)=O.[CH2:41]([Si:49]([CH3:55])([CH3:54])[O:50][SiH:51]([CH3:53])[CH3:52])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>[Pt].C1(C)C=CC=CC=1>[CH2:1]([Si:51]([CH3:52])([CH3:53])[O:50][Si:49]([CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([CH3:55])[CH3:54])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 7501Styrene2×HCID 7918Acetic AnhydrideHCID 186591,1,3,3-Tetramethyl-disiloxaneHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 125730908HCID 125730908, compound

Product 1

HCID 114278561,1,3,3-TETRAMETHYL-1,3-DI(2-PHENYLETHYL) DISILOXANEYield 58%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

380 mg Of styrene and 240 mg of 1,1,3,3-tetramethyldisiloxane were placed in a glass tube to which 20 μL (21.6 mg) of acetic anhydride and 2 μL (2.3 mg) of triisopropylsilyl trifluoromethanesulfonate (i-Pr3SiOSO2CF3) were added by microsyringe. 5 μL (platinum weight: 0.0017 mg) Of a toluene solution (platinum content: 0.04 wt %) of zero-valent platinum complexed with divinylsiloxane were added to this. The tube was put in a 60° C. oil bath and heated for 8 hours. After cooling, the tube contents were analyzed by gas chromatography, which revealed that the styrene conversion rate was 55%, 1-phenethyl-1,1,3,3-tetramethyldisiloxane had been produced at a yield of 58% (based on 1,1,3,3-tetramethyldisiloxane) and 1,3-bis(phenethyl)-1,1,3,3-tetramethyldisiloxane at a yield of 21%, and the ratio of alpha addition to beta addition of phenethyl groups was 1:49.

Workup

  1. additionwere added by microsyringe
  2. additionwere added to this
  3. customwas put in a 60° C.
  4. temperatureheated for 8 hours
  5. temperatureAfter cooling

Sources & evidence

ORD record
ord-f6c28f084f244659b617837f722b3dab
Source dataset
uspto-grants-2001_10
Patent number
US06297340B1

Reaction notes

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