A novel stereochemical control : A persistent preference for exo electrophile acceptance in 2-bornanes

The conjugate bases of camphor oxime and 2-nitro-bornane, possessing a π array, accept elements of H⁺ and Br⁺ selectively from the “crowded” exo side. The present work adds another facet towards the understanding of stereochemical controls inherent in the bornane framework, the other two related being the endo addition of nucleophiles to camphor and the exo electrophile acceptance by camphor enolates. The present work describes, inter alia, a practical route to 2-endo nitrobornane and the novel 2,2-dinitrobornane.