Table 1.
Oxidations of methyl phenyl sulfide a.
| Entry | H2O2
(mmol) |
Solvent (2 mL) |
Time (min) | Temp. (oC) | Conversion (%) b |
Sulfoxide Selectivity (%) b |
|---|---|---|---|---|---|---|
| 1 | 8 | CH3COOH | 80 | 25 | 100 | >99 |
| 2 | 8 | CH2Cl2 | 90 | 25 | 0 | 0 |
| 3 | 8 | CH3CN | 90 | 25 | <5 | >99 |
| 4 | 8 | CH3NO2 | 90 | 25 | <5 | >99 |
| 5 | 8 | CH3OH | 240 | 25 | 20 | >99 |
| 6 | 8 | CH3COOH | 440 | 0 | 93 | >99 |
| 7 | 8 | CH3COOH | 35 | 45 | 100 | >99 |
| 8 | 8 | CH3COOH | 20 | 60 | 100 | >99 |
| 9 | 8 | CH3COOH | 8 | 80 | 100 | >99 |
| 10 | 1 | CH3COOH | 80 | 25 | 8 | >99 |
| 11 | 2 | CH3COOH | 80 | 25 | 13 | >99 |
| 12 | 5 | CH3COOH | 80 | 25 | 23 | >99 |
| 13 | 8 | CH3COOH | 80 | 25 | 100 | >99 |
| 13 | 10 | CH3COOH | 75 | 25 | 100 | >99 |
| 14c | - | CH3COOH | 600 | 25 | 7 | >99 |
a In all experiments 2 mmol of substrate were used.
b Isolated yield on the basis of the weight of the pure product obtained.
c The reaction was carried out under an atmosphere of O2 instead of in the presence of 30% H2O2.