Alkenes triethylsilyl hydrotrioxide reactions

A mechanism was proposed to account for the reaction of triethylsilyl hydrotrioxide with electron-rich alkenes as a dioxetane-forming process (route a equation 82) and with inactivated alkenes as a nondioxetane carbonyl-forming process (route b equation 83). 

Reaction of triethylsilyl hydrotrioxide with electron-rich olefins to give dioxetanes that react intramolecularly with a keto group in the presence of t-butyldimethyl silyl triflateto afford 1,2,4-trioxanes also oxydative cleavage of alkenes. Also used in cleavage of olefins (see 1st edition)... 

Alkene Oxidation Reactions. The reaction of triethylsilane with ozone and use of the intermediate triethylsilyl hydrotrioxide in oxidation reactions have been described. Initial oxidation reactions reported included the formation of the 9,10-endoperoxide from 9,10-dimethylanthracene (eq 1), and an allyUc hydroperoxide from 2,3-dimethyl-2-butene (eq 2). Researchers also observed a near-IR emission from triethylsilyl hydrotrioxide as it decomposed at —60°C, consistent with generation of singlet oxygen. Other workers have characterized triethylsilyl hydrotrioxide by NMR spectroscopy and and measured the kinetics of its decomposition in deuterated acetone. ... 

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