Chiral liquid crystalline nitrones were synthesized from opticallly active 2-methyl-1-butanol in a four step sequence involving 1) conversion to alkyl bromides, 2) a base catalyzed SN2 reaction with p-nitrophenol, 3) reduction to the corresponding hydroxylamine with zinc/ammonium chloride and 4) condensation with p-alkoxy benzaldehydes (alkyl = normal C1-C8). For alkyl = 5-8 new chiral smectic C mesophases were produced with polygonal textures, high viscosities and high smectic C-isotropic transition enthalpies. The nitrones were quantitatively isomerized to non-mesomorphic amides upon irradiation at 330 mu, presumably through the intermediacy of oxaziranes which thermally convert to the amides. Spectroscopic evidence for the oxazirane intermediates was presented.