Journal of the American Chemical Society

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

W Adam, M Heil

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

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被引用次数: 34

摘要

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 ...