Macrocyclic Polylactams of Mirror Symmetry: Preparation and Structure

Article abstract of DOI:10.1021/jo00350a005

The synthesis and structure of a series of macrocyclic lactams possessing reflection symmetry are described.The synthesis involves condensation of diazasilolidines 1 and 2 with diacyl dihalides 3 to give either exclusively macrocyclic dilactams 4 or tetralactams 5.The high product selectivity of these reactions is attributed to noncovalent interactions between silicon and carbonyl oxygen.The structures of the macrocyclic lactams prepared are analyzed by high-resolution 1H and 13C NMR spectrometry as well by X-ray diffraction studies.The observed conformational regularities are discussed and compared with those of macrocyclic lactams of rotational symmetry.