Table 1. Base-dependent synthesis of three regioisomers of singly bridged calix[6]crown-6.
Reaction conditions: calix[6]arene (1.0 equiv), base (2.0 equiv), pentaethylene glycol ditosylate (0.9 equiv), xylene (500 ml), reflux. Selectivity ratios were determined by 1H NMR.
| Selectivity ratio (%) | ||||
|---|---|---|---|---|
| Base | H4 L 1,2 | H4 L 1,3 | H4 L 1,4 | Total yield (%) |
| Na2CO3 | 75 | 15 | 10 | 32.4 |
| K2CO3 | 49 | 43 | 8 | 33.6 |
| Rb2CO3 | 17 | 22 | 61 | 32.5 |
| Cs2CO3 | 0 | 17 | 83 | 35.9 |