Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions

The synthesis and characterisation, including solid state structure, of a macrocycle containing both a hydrazone and a disulfide linkage is described. Selective ring-opening of the macrocycle under thermodynamic control could be achieved at either the disulfide or the hydrazone linkage by applying mutually exclusive sets of reaction conditions.