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Effect of reaction conditions on H-D exchange.a
| ||||
|---|---|---|---|---|
| Entry | 1 (mol%) | AgTFA (mol%) | solvent | % D |
| 1 | 10 | 10 | CF3COOD | 86 |
| 2 | 10 | 20 | CF3COOD | 82 |
| 3 | 5 | 5 | CF3COOD | 72 |
| 4b | 10 | 10 | CF3COOD | 9 |
| 5c | 10 | 10 | CF3COOD | 77 |
| 6d | 10 | 10 | CF3COOD | 76 |
| 7 | 10 | 10 | DOAc-d3 | 0 |
| 8 | 10 | 10 | MeOD-d3 | 1 |
| 9e | 10 | 10 | CF3COOD | 85 |
H-D exchange of other aromatic positions has been omitted for clarity.
Reaction conducted at 60 °C.
0.5 mL of CF3COOD was added.
2 mL of CF3COOD was added.
Reaction proceeded for 36 h.
