Triethylsilane → (Z)-alpha-triethylsilyl-beta-methylstyrene
Reaction equation
[C:1]1([C:7]#[C:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([SiH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH3:11].C([Si](CC)(CC)/C(/C)=C\C1C=CC=CC=1)C>>[CH2:10]([Si:12]([CH2:15][CH3:16])([CH2:13][CH3:14])/[C:7](/[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:8]\[CH3:9])[CH3:11]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 0.125 ml (1.0 mmol) of 1-phenylpropyne, 0.192 ml (1.2 mmol) of triethylsilane, and 5.2 mg (0.01 mmol) of tetraethylammonium μ-hydridebis(pentacarbonylchromium) was heated in a sealed tube at 100° C. for 16 hours while being stirred. GLC analysis of the reaction mixture revealed that (Z)-β-triethylsilyl-β-methylstyrene and (Z)-α-triethylsilyl-β-methylstyrene were produced in a yield of 95% and 2%, respectively, with no production of other isomers.
Sources & evidence
- ORD record
- ord-68a3adef7deb42a1ab5c9e37d482b7b8
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05182246
Reaction notes
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