Substituent Effect in the Synthesis of α,α‐Dibromoketones, 1,2‐Dibromalkenes, and 1,2‐Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid

Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α‐dibromoketone and 1,2‐diketone derivatives. Diarylalkynes with activating groups provided 1,2‐diketone derivatives as the major products, whereas diarylalkynes with a non‐activating group or alkylarylalkynes gave α,α‐dibromoketo...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-04, Vol.361 (8), p.1846-1858
Main Authors: Cho, Eunjeong, Jayaraman, Aravindan, Lee, Junseong, Ko, Kyoung Chul, Lee, Sunwoo
Format: Article
Language:English
Subjects:
1,2-dibromoalkene
1,2-diketone
alkyne
Alkynes
Deactivation
Density functional theory
Derivatives
DFT calculation
Diketones
α,α-dibromoketones
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Summary:Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α‐dibromoketone and 1,2‐diketone derivatives. Diarylalkynes with activating groups provided 1,2‐diketone derivatives as the major products, whereas diarylalkynes with a non‐activating group or alkylarylalkynes gave α,α‐dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2‐dibromoalkenes. The reaction was conducted at room temperature and showed good yields in most cases. Reaction pathways have been proposed on the basis of experimental observations and density functional theory (DFT) calculations.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801535