Synthesis of d-mannitol and l-iditol derivatives as monomers for the preparation of new regioregular AABB-type polyamides

1,6-Diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl-d-mannitol (and its l-iditol analogue) suitable for their utilization as monomers in the preparation of linear polyamides are described. Regio- and stereoregular polyamides of the AABB-type have been prepared by the active ester polycondensation method from these C2 symmetric monomers and suberic and dodecanedioic acids. The resulting polyamides were obtained in fair yields (70–60%) and were characterized by elemental analyses and infrared and 1H and 13C NMR spectroscopies. Their Mw and Mw/Mn were determined by GPC relative to polystyrene standards. All of them were gummy non-crystalline solids.