Radical cyclizations involving the evolution of nitrogen

Abstract

The radical cyclizations of N-aziridinyl imines and alkyl azides provided reliable methods for the formation of five- and six-membered carbon-centered and nitrogen-centered radicals from acyclic precursors. N-Aziridinyl imino and azido groups were utilized as radical precursors as well as radical acceptors in radical cyclization. Furthermore, intramolecular addition of aminyl radicals to carbonyl groups proceeded cleanly, yielding 1,5-acyl group transfer from carbon to nitrogen.