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Synthesis of Isoxazoline/Cyclic Nitrone-Featured Methylenes Using Unsaturated Ketoximes: A Dual Role of TEMPO

2016/03/08 by Fei Chen, Xiu-Long Yang, Xiu‐Long Yang +3 · 3 citations
Chemistry · #Catalysis #Catalytic C–H Functionalization Methods #Chemistry #Combinatorial chemistry #Cycloaddition #Dual (grammatical number) #Dual role #Nitrone #Organic chemistry #Polymer #Radical Photochemical Reactions #Radical initiator #Regioselectivity #Synthesis and Catalytic Reactions #Tandem

paper · doi:10.1021/acs.joc.6b00180

openalex publication_date 2016/03/08 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

A novel, metal-free, and regioselective approach for the synthesis of isoxazoline/cyclic nitrone-featured methylenes has been developed by the reaction of readily accessible β,γ- and γ,δ-unsaturated ketoximes with TEMPO via tandem iminoxyl radical-promoted cyclization/TEMPO-mediated Cope-like elimination, respectively. This protocol utilizes commercially available TEMPO as the iminoxyl radical initiator as well as the β-hydrogen acceptor in the Cope-like elimination.

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