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Relationship between reaction conditions and E/Z ratios for the addition of methimazole to propiolate esters.
| Reactant | Reaction Conditions | E/Z ratio |
|---|---|---|
| Methyl propiolate | RT, Et3N | 1.1:1 |
| Methyl propiolate | RT, DABCO | 8:1 |
| Methyl propiolate | RT, DABCO, dropwise addition of ester | 7.4:1 |
| Methyl propiolate | −20°C, DABCO | 8:1 |
| tert-Butyl propiolate | RT, DABCO | 60:1 |
| tert-Butyl propiolate | −15°C, DABCO | 70:1 |
