Oxidative functionalization of alkylidenecyclopropanes and alkylidenecyclobutanes: a versatile platform to access nitrated cyclopropanes and cyclobutanes.

A divergent radical nitration of alkylidenecyclopropanes (ACPs) and alkylidenecyclobutanes (ACBs) with Fe(NO3)3·9H2O or AgNO2 has been achieved, affording three categories of products including β-nitro alcohol, α-nitro ketone and nitro nitratosation products with yields up to 90%. Particularly, the cyclopropyl and cyclobutyl rings were conserved in the products. The applicability of this method was demonstrated by the scale-up experiment and reduction of the nitro into an amino group. Preliminary mechanistic studies suggested that the nitro radical was involved in the reaction process.