Collect. Czech. Chem. Commun. 1993, 58, 354-364

Oxidizability and Structure of Lactams

Jaroslav Burda and Božena Lánská

Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, 162 06 Prague 6, Czech Republic


The radical-initiated chain oxidation of five- to nine-membered lactams with molecular oxygen has been studied by the quantum-chemical method AM1. It has been confirmed that the reaction is controlled by its propagation step. The kinetic length of the oxidation chains correlates with the energy of formation of the lactam radical by abstraction of hydrogen from the methylene group adjacent to nitrogen atom. With five- to eight-membered rings the reaction is symmetry-forbidden.