1.2- Dioxetanes nucleophilic substitution

Besides thermal and photolytic decompositions of 1,2-dioxetanes, there has been relatively little other chemistry explored with these high energy molecules. Several nucleophilic substitution reactions have been documented. 

Alkylthio- or arylthio-substituted 1,2-dioxetanes derived from an adamantylidene vinyl system (29) undergo attack by appropriate oxygen nucleophiles in the presence of Lewis acid to form alkoxy-, aryloxy-, or acyloxy-substituted 1,2-dioxetanes (32).24 A novel, S N 1 reaction mechanism was suggested, involving species (30) and (31). 

An interesting approach to 1,4,22 -dioxaphosphinanes has been reported. Methyl-substituted 1,2-dioxetans (357) react with triphenylalkylidenephosphoranes (358) by nucleophilic attack of the ylide carbon at the peroxide bond of (357) the 2,2,2-triphenyl-1,4,22 -dioxaphosphinanes (360) are... 

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