Dioxetanes with triphenyl phosphite ozonide

Several ketenes have been converted into l,2-dioxetan-3-ones by reaction with triphenyl phosphite ozonide (77JA5836), and ketenimines form cyclic iminoperoxides with photochemi-cally generated singlet oxygen (Scheme 97) <79AG(E)788,80CC898). 

Biadamantylene dissolved in methylene chloride at -78 °C and treated with a solution of triphenyl phosphite ozonide in the same solvent and subsequently with a mixture of methanol and pyridine gives biadamantylene dioxetane in 91% yield (equation 64). The dioxetane decomposes at 150 °C [1101]. 

The ozonide is also able to imitate another reaction of singlet oxygen 1,2-cycloaddition to vinylene diethers to yield 1,2-dioxetanes.4 However, there is one difference. Singlet oxygen reacts stereospecifically with cis- and trans-diethoxyethylene, (5) and (7), to give (6) and (8), respectively. Triphenyl phosphite... 

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