Miscellaneous reduction procedures

G Cainelli, F Manescalchi, A Umani-Ronchi and M Panunzio, J. Org. Cliem., 1978,43, 1598. 

Selected examples of the conversion of sulphilimines and sulphoximines into disulphides  

Sulphoxides and sulphoximines are reduced to thioethers by similar reaction sequences [3, 4], In most cases, the yields of the thioethers are higher ( 70%) from the diaryl compounds, than from dialkyl or aryl alkyl derivatives but, when the reductions are conducted in an excess of chloroform, the yields of the thioethers are diminished [3], This observation suggests that the thioethers are reacting with dichlorocarbene and that the dialkyl and aryl alkyl compounds are more susceptible than the diaryl derivatives (Table 11.20). 

Compared with the sulphinimines, the A -tosylsulphinimines are less readily reduced and, to obtain acceptable yields, it is necessary to use larger amounts of catalyst. This suggests that the A-tosyl derivatives may be hydrolysed to the sulphinimines prior to the electrophilic attack by the carbene. 

---

Amongst the miscellaneous procedures by which phenols have been derived may be mentioned the catalytic reduction of a cumene nuclear hydroperoxide with hydrogen and Pd/AljOj under a slight pressure for 5 hours at less than... 

---