Reaction of 1, 2-dioxetanes with heteroatom nucleophiles: adduct formation by nucleophilic attack at the peroxide bond

W Adam, M Heil

Index: Adam, Waldemar; Heil, Markus Journal of the American Chemical Society, 1992 , vol. 114, # 14 p. 5591 - 5598

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Citation Number: 34

Abstract

Abstract: The reactions of 3, 3-disubstituted 1, 2-dioxetanes. l with numerous heteroatom nucleophiles, eg, R2NH, R3N, RSH, R2S, CN-, SCN-, Br-, C1-, OH-, and 02'-, were investigated. Initial nucleophilic substitution at the sterically less hindered site of the dioxetane peroxide bond leads to addition, deoxygenation, and fragmentation products. The observed sN2 chemistry was substantiated with the dioxetane IC because bromide ion ...