Abstract
The reactions of 3,3-disubstituted 1,2-dioxetanes 1 with numerous heteroatom nucleophiles, e.g., R 2 NH, R 3 N, RSH R 2 S, CN - , SCN - , Br - , Cl - , OH - , and O 2 .- , were investigated. Initial nucleophilic substitution at the sterically less hindered site of the dioxetane peroxide bond leads to addition, deoxygenation, and fragementation products. The observed S N 2 chemistry was substantiated with the dioxetane 1c because bromide ion displacement by the proximate alkoxide ion site afforded epoxide products
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