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Updated: Oct 25, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Visible Light-Mediated Dearomative Remote Functionalization of Arenes via a Tandem Strain-Release Spirocyclization
Apurba Samanta1, Soumitra Maity1
1Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, Dhanbad, Jharkhand826004, India.
Abstract:
Tandem strain-release addition cyclization reactions in bicyclo[1.1.0]butanes (BCBs) present a versatile platform for rapidly creating molecular complexity. While lactams and indolinones have been accessed using alkenes and arenes as appendages via this strategy, the dearomative functionalization of arenes remains unexplored. This work demonstrates a photocatalyst-free, visible light-mediated blueprint for the remote functionalization of arenes in tandem with a strain-release framework. Nitrosamines are utilized as versatile reagents for installing sulfonamides and oximes, leading to intricately designed 3D spirocyclic structures bearing medicinally relevant functionalities.
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