Synthesis of Novel Sustainable Oligoamides Via Ring-Opening Polymerization of Lactams Based on (-)-Menthone

In the context of novel sustainable and structurally significant building blocks for polymer science, the synthetic routes are described to new oligoamide structures based on the terpenoid ketone (-)-menthone. The basic concept is an oxime formation of this cyclic ketone followed by the Beckmann rearrangement, resulting in the corresponding lactams. These lactams are polymerized under anionic or acid-catalyzed conditions (ring-opening polymerization (ROP)) to give alkyl-substituted and stereocenter containing oligoamide scaffolds that are assumed to be suitable for further copolymerizations and modifications and thus for a wide range of different applications. The regio- and the stereochemistry of the formed oximes and lactams as well as their impact on the polymerization behavior is discussed.