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Updated: May 13, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
A vinylcyclobutane substrate designed as a cyclopropylcarbinyl radical probe
Phyllis A Leber1, Ryan M Bell, Carlton W Christie
1Department of Chemistry, Franklin & Marshall College, Lancaster, PA, USA. phyllis.leber@fandm.edu
Abstract:
Appending a spirocyclopropane linkage to bicyclo[3.2.0]hept-2-ene is achieved by selective kinetic cyclopropanation of 6-methylenebicyclo[3.2.0]hept-2-ene. The resultant vinylcyclobutane undergoes [1,3] migration as the dominant thermal process. A minor cyclopropylcarbinyl (CPC) rearrangement product clearly implicates a diradical transition structure. The presence and absence of other potential thermal products have enabled us to construct a detailed mechanistic proposal to account for all viable dynamic processes.
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