Remodelling of Tricyclic Carbon Frameworks with a Norbornene Scaffold

Abstract

We describe a halogen/chalcogen-mediated skeletal rearrangemnt of tricyclo[4.3.0.03,7]non-8-ene derivatives that feature a norbornene framework with two hydroxy/silyloxy groups substituted on the bridgehead carbons, yielding a tricyclo[4.2.1.03,7]nonane (brendane) skeleton. Four different types of consecutive Pd(II)-mediated skeletal rearrangement/C–C cross-coupling reactions are further demonstrated.