title: A vinylcyclobutane substrate designed as a cyclopropylcarbinyl radical probe.
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.
authors: Department of Chemistry, Franklin & Marshall College, Lancaster, PA, USA. phyllis.leber@fandm.edu
authors: Phyllis A
authors: PA
authors: Leber
authors: Ryan M
authors: RM
authors: Bell
authors: Carlton W
authors: CW
authors: Christie
authors: Joseph A
authors: JA
authors: Mohrbacher
mesh_terms: D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D015195:Drug Design; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D013379:Substrate Specificity; D013816:Thermodynamics
chemical_list: D003503:Cyclobutanes; D003521:Cyclopropanes; D005609:Free Radicals