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Reaction id: 0801011021_20, verified by Personal Chemistry ©
Trans-stilbene oxide
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Piperidine
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Bi(OTf)3*4 H2O
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prod (2) (2) (2)
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Yield: 100% Time: 900s Temperature: 160 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 1439-07-2 |
196.249 |
1.000 |
1.000 |
196.249 mg |
| 110-89-4 |
85.150 |
0.861 |
1.100 |
108.786 µl |
| Bi(OTf)3*4 H2O |
728.238 |
1.000 |
0.010 |
7.282 mg |
| Product 1 |
281.399 |
1.000 |
0.000 |
0.000 mg |
Keywords
Amination, Catalysis, Catalyzed, Metal, N-Alkylation, Nucleophilic, Ring opening, Solvent-free, Substitution, Epoxide opening
Comments
Synthesis: The reaction can also be carried out with other metal triflates (Sc, Ga, Zn were tried) and with HOTf. It worked well with a number of amines, but gave significantly lower yields with non-cyclised dialkylamines. The reaction was carried out at 1 mmol scale, but could be scaled up to 30 mmol with no loss in yield. The method also worked for styrene oxide as starting material, but then two regioisomers were formed.
Work-up and purification: After the reaction, 1 ml diethyl ether or ethyl acetate was added and the solution filtered through a pad of celite. The celite was washed with 1 ml diethyl ether or ethyl acetate and the combined solution was concentrated to give the pure product.
Characterisation: By 1H NMR.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Ollevier, T.; Nadeau, E. Tet. Lett. 2008, 49, 1546-1550
Analysis
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