Separating cis/trans isomers of diazo compounds using thin-layer chromatography (TLC) is challenging due to their structural similarities and the limitations of TLC in sample collection. Liquid chromatography (LC) is a more viable alternative, utilizing a suitable stationary phase, typically silica gel, and an appropriate mobile phase tailored to the compounds' polarity. For polar diazo compounds, a 70:30 acetonitrile/water mobile phase may be effective. Adjusting the mobile phase's polarity by altering solvent ratios can enhance separation, with pressurization of the column potentially increasing efficiency. While theoretically possible to separate these isomers with the right conditions, significant challenges remain, especially if the isomers are very similar, necessitating advanced techniques like High Performance Liquid Chromatography (HPLC) for effective separation.