Application of MICCS-NMR #1 Reaction pathway analysis of radical addition
NM060006E
Reaction
This note treats triethylborane(Et3B)-mediated radical addition to oxime ether, where a borane complex is proposed as a key intermediate. However, its isolation is very difficult using conventional methods.
Sample is by courtesy of Prof. T. Naito, Prof. O. Miyata,
and Dr. M. Ueda of Kobe Pharmaceutical University.
Protocol of NMR measurements
NMR spectra are observed throughout the reaction, which is initiated by cotroling the flow rate of the individual reactants. When the concentration ratio of oxime ether and Et3B becomes 1 to 1, CH3OH is added.
Thereby, spectra yield signals of reactants, intermediate, and product, sequentially.
| 1M oxime ether | 1M Et3B | 1M CH3OH |
| 10.0 | 0.5 | 0.0 |
| 9.0 | 1.0 | 0.0 |
| 8.0 | 2.0 | 0.0 |
| 7.0 | 3.0 | 0.0 |
| 6.0 | 4.0 | 0.0 |
| 5.0 | 5.0 | 0.0 |
| 5.0 | 5.0 | 0.5 |
| 4.5 | 4.5 | 10. |
| 4.0 | 4.0 | 2.0 |
| 3.5 | 3.5 | 3.5 |
| 2.0 | 4.0 | 2.0 |
| 1.0 | 5.0 | 5.0 |
＊CH2Cl2signal is suppressed.
JNM-ECA500
Accumulation: 16scan
Recycle delay: 10s
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