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Reaction id: 0601011043_02, verified by Personal Chemistry ©
1b
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NaI
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MeCN
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2b
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Yield: 94% Time: 600s Temperature: 200 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| Substrate 1 |
343.445 |
1.000 |
0.100 |
34.345 µl |
| NaI |
149.894 |
1.000 |
0.200 |
29.979 mg |
| MeCN |
41.053 |
0.780 |
57.000 |
3000.000 µl |
| Product 1 |
343.445 |
1.000 |
0.000 |
0.000 µl |
Keywords
Heterocyclic, Heterocyclisation, Rearrangement, Ring closure, Ring formation, Ring opening, SN2'
Comments
Synthesis: The stereochemistry of this reaction was studied by using stereochemically pure starting materials (both the cis and trans one) separately. Both reactions gave the same product, and substrate mixtures gave stereochemically pure product. Both LiI and NaI were used and gave good results, whereas no product was formed when the iodide was omitted.
Work-up and purification: After the reaction, the solvent was removed and the product purified by column chromatography.
Characterisation: By mp, IR, 1H NMR, 13C NMR and MS.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Hirner, S.; Somfai, P. Synlett 2005, 3099-3102
Analysis
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