CIDNP study and ab-initio calculations of rigid vinylcyclopropane systems: Evidence for delocalized 'ring-closed' radical cations

Article abstract of DOI:10.1016/S0040-4020(97)00347-5

The radical cations of three terpenes, sabinene, 1, and α-, 2, and β-thujene, 3, containing vinylcyclopropane functions held rigidly in either an anti- or syn-orientation, have been elucidated by CIDNP studies. The structures assigned to these species are discussed in view of their reactivities and compared with three simplified radical cations, 2-methylenebicyclo[3.1.0]hexane, 4, bicyclo[3.1.0]hex-2-ene, 5, and 5-methylbicyclo[3.1.0]hex-2-ene, 6, calculated by ab initio molecular orbital methods.