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Reaction id: 0801011012_10, verified by Personal Chemistry ©
Phenyl azide
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1-Ethynyl-1-cycl...
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[Cp*RuCl]4
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DMF
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3_3
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Yield: 72% Time: 1200s Temperature: 110 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 622-37-7 |
119.127 |
1.000 |
1.100 |
131.040 mg |
| 78-27-3 |
124.183 |
0.976 |
1.000 |
127.198 µl |
| [Cp*RuCl]4 |
1087.010 |
1.000 |
0.025 |
27.000 mg |
| DMF |
73.095 |
0.940 |
77.160 |
6000.000 µl |
| Product 1 |
243.310 |
1.000 |
0.000 |
0.000 mg |
Keywords
1,3 Dipolar addition, Catalysis, Catalyzed, Cyclisation, Cycloaddition, Heterocyclic, Heterocyclisation, Metal, Ring closure, Ring formation
Comments
Synthesis: In the development of this method, [Cp*RuCl]4 (pentamethylcyclopentadienyl ruthenium(II) chloride tetramer) was found to be superior to Cp*RuCl(PPh3)2. Acetonitrile could also be used as solvent, but gave significantly lower yields. Increasing the reaction time or temperature did not increase the yields obtained.
The reaction vial was flushed with nitrogen before it was capped and heated.
Work-up and purification: After the reaction, 20 ml each of ethyl acetate and water were added to the mixture. The organic phase was collected and the water phase washed with 2*20 ml ethyl acetate. The combined organic fractions were washed with brine, dried (MgSO4) and the solvent removed under reduced pressure. The product was isolated by flash chromatography (silica eluted with ethyl acetate/hexane 1/6).
Characterisation: By mp, 1H NMR, 13C NMR and MS.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Rasmussen, L. K.; Boren, B. C.; Fokin, V. V. Org. Lett. 2007, 9, 5337-5339
Analysis
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