I tried a variety of solvent systems to no avail. Given the structure of the starting material, what should be the best solvent system to avoid tailing.
Tailing in TLC is due to the molecule not being 'happy' in the solvent system. That is there is a partial retention or interaction between the molecule, the stationary support, and the solvent. Most TLC solvents are organic but they can be classified as polar or non-polar. To prevent hydrogen bonding... use only very non-polar solvents which contain no organic acids or alcohols, like Hexane.
Your TLC plates are having silica coated on plates. Silica is polar molecule with large number of -OH groups. If the molecule is being retained on the silica (in the form of tail)..the tail can only be avoided by replacing your solvent with non-polar solvent like hexane, pet ether etc. or if you are using combination of solvents, then increase the ratio of non-polar solvent.
What is the Stationary Phase? Usually this type of problems can be solved trying with different solvent systems.
Good luck
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