Table 1.
Stability of vinyl ethers 1a–e and their decaging with tetrazine 2a.
| Compound[a] | Alcohol[c] | Pyridazine[c] | Conversion | Stability[d] |
|---|---|---|---|---|
| 1a[b] | 61% | 49% | 100% | 100%[e] |
| 1b | 68% | 65% | 73% | 100% |
| 1c | 57% | 72% | 100% | 77% |
| 1d | 50% | 47% | 56% | 100% |
| 1e | 65% | 50% | 100% | n.d.[f] |
[a]
The reactions were performed in dichloromethane at room temperature with 1 equiv. of vinyl ether (100 mM) 1a–e and 2 equiv. of tetrazine 2a (200 mM) for 72 hours.
[b]
The reaction was complete after 40 hours.
[c]
Yield of isolated product.
[d]
The stability (as % of remaining starting compound) was assessed by HPLC in PBS pH 7.4 at 37 °C with a concentration of vinyl ether of 200 μM using acetophenone as an internal standard.
[e]
10% H2O in DMF.
[f]
1e does not absorb in the UV. n.d., not determined.