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• W2955480939 endingPage "9057" @default.
• W2955480939 startingPage "9051" @default.
• W2955480939 abstract "Aryl carbamates are orthometalated by sodium diisopropylamide (NaDA) in tetrahydrofuran. The resulting arylsodiums undergo Snieckus–Fries rearrangement to give orthoacylated phenols in good yield. The intermediate arylsodiums and resulting orthoacylated phenolates are suggested to be monomeric. The rate-limiting step in the two-step sequence depends on the steric demands of the carbamoyl moiety and the substituents in the meta position of the arene. Rate studies reveal a dominant disolvated-monomer-based orthometalation followed by a di- or trisolvated arylsodium monomer-based rearrangement. Kinetic evidence of a NaDA-catalyzed Snieckus–Fries rearrangement suggests the intermediacy of mixed trimers. Competitive halide eliminations to form benzyne are also discussed." @default.
• W2955480939 created "2019-07-12" @default.
• W2955480939 creator A5008735740 @default.
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• W2955480939 date "2019-07-01" @default.
• W2955480939 modified "2023-10-12" @default.
• W2955480939 title "Aryl Carbamates: Mechanisms of Orthosodiations and Snieckus–Fries Rearrangements" @default.
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• W2955480939 doi "https://doi.org/10.1021/acs.joc.9b00968" @default.
• W2955480939 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/7050188" @default.
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• W2955480939 hasPublicationYear "2019" @default.
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