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Updated: Sep 27, 2025
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes
Amanda Bunyamin1, Carol Hua1,2, Anastasios Polyzos1,3
1School of Chemistry, University of Melbourne Parkville Victoria 3010 Australia daniel.priebbenow@unimelb.edu.au.
Abstract:
Visible light induced singlet nucleophilic carbenes undergo rapid [2 + 1]-cycloaddition with tethered olefins to afford unique bicyclo[3.1.0]hexane and bicyclo[4.1.0]heptane scaffolds. This cyclopropanation process requires only visible light irradiation to proceed, circumventing the use of exogenous (photo)catalysts, sensitisers or additives and showcases a vastly underexplored mode of reactivity for nucleophilic carbenes in chemical synthesis. The discovery of additional transformations including a cyclopropanation/retro-Michael/Michael cascade process to afford chromanones and a photochemical C-H insertion reaction are also described.
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