Experimental and Theoretical Investigations of the Bromination of Phenols with β and γ Aliphatic Substituents, including Rings

Bromination reactions of substituted and ring fused phenols were studied by both experiment (t-BuNH-Br) and computation (density functional theory). The outcomes support each other, indicating a clear and predictable regioselective preference among 3,4-bis-alkylated and 3,4-ring-fused phenols.

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Bibliographic Details
Published in:Journal of organic chemistry 2015-09, Vol.80 (18), p.9292-9296
Main Authors: Zhang, Jinsong, Chang, Xiao, Bowman, Erich C, Holt, Carter J, Lodewyk, Michael W, Miller, Randy M, Xia, Guangming
Format: Article
Language:English
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Summary:Bromination reactions of substituted and ring fused phenols were studied by both experiment (t-BuNH-Br) and computation (density functional theory). The outcomes support each other, indicating a clear and predictable regioselective preference among 3,4-bis-alkylated and 3,4-ring-fused phenols.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01866