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Updated: Nov 2, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Three-Component Radical Iodonitrosylative Cyclization of 1,6-Enynes under Metal-Free Conditions
Shaoqun Zhu1, Qi Cheng1, Haibo Yang1
1School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, 225009, China.
Abstract:
A three-component, metal-free radical cascade iodonitrosylative cyclization reaction was described. The nitroso radical was generated from tert-butyl nitrite and triggered the radical addition/cyclization/iodination/oxidation sequences. A variety of 1,6-enynes were tested and proved to be compatible, delivering various highly functionalized hetero- and all-carbon cycles and nitro and vinyl C-I bonds containing pyrrolidines, tetrahydrofuran, and cyclopentane in moderate to excellent isolated yields.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.