Sulphonyl Peroxides

Sulphonyl Peroxides.—Continuing interest in this class of compound is a consequence of their value in aromatic sulphonoxylation and in their addition to alkenes to give sulphonate esters. A useful electrochemical preparation of bis(methanesulphonyl) peroxide from sodium methanesulphonate makes available a reagent for the synthesis of methanesulphonates of less reactive aromatic hydrocarbons. 

Stereoselective addition of nitrobenzene-p-sulphonyl peroxide to cis- and /mnj-stilbenes has been studied. Random ratios of meso- and /-adducts were obtained, and it was concluded that the carbonium ion intermediate in the electrophilic addition process is sufficiently long-lived in this case to undergo rotation before capture.  

---

Acetyl cyclohexane-sulphonyl peroxide (28% phthalate solution) o-Azidobenzoyl peroxide t-Butyl mono permaleate (95% dry) t-Butyl peracetate (70%) t-Butyl peractoate... 

Acetyl cyclohexane-sulphonyl peroxide (28% phthalate solution)... 

Primary and secondary amines are also oxidized to aldehydes and ketones, via imines, using sulphonyl peroxides. The first reports of high-yield selective oxidative conversions of unbranched primary amines into em-dihalides (masked aldehydes) have appeared (Scheme 9), and the cleavage of tertiary amines to carbamates with ethyl chloroformate has been examined. ... 

---