The synthesis of two series of liquid crystalline polyoxiranes and polyoxetanes containing 4-(4-hydroxybiphenyl-4′-carbonyloxy)- phenyl (2S,3S)-2-chloro-3-methylvalerate side groups is presented. Differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction measurements reveal liquid crystalline phases for all obtained polymers. A majority of the prepared polyoxiranes present cholesteric, smectic A, chiral smectic C and an undefined smectic phases. Most of the prepared polyoxetanes reveal only a chiral smectic C phase. Effect of polymer backbone and spacer length on the mesomorphic properties of the obtained polymers is discussed. Although the polyoxirane and polyoxetane backbone are more flexible than the polymethacrylate backbone, side-chain crystalization does not occur in any of the synthesized polymers.