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Comparison of the reactivity of TMSCl and TMSBr.
| Dialkyl Phosphonate RP(O)(OR′)2 |
TMSCl | TMSBr | |||||||
|---|---|---|---|---|---|---|---|---|---|
| R | R′ | Equiv. | Temp. (°C) |
Time (days) |
Yields (%) |
Equiv. | Temp. (°C) |
Time (h) |
Yields (%) |
| CH2=CH | Et | 2.7 | 69–72 | 5 | 94 | 1.5 | 25 | 1.2 | >99 |
| PhCH2 | Et | 2.2 | 40 | 1 | <5 | 1.7 | 25 | 2.0 | >99 |
| EtOCH2CH2 | Et | 2.9 | 40 | 1 | <10 | 1.7 | 25 | 0.7 | >99 |
| Cl3C | Et | 5.4 | >72 | 8 | 13 | 1.5 | 61–69 | 2.7 | >99 |
| PhC(O) | Me | 1.9 | 25 | 9 | 12 | 1.5 | 25 | 1.7 | >99 |
