Several approaches for synthesizing phenyliodine dicarboxylate compounds were compared by the yield and purity of desired products. One methodology employed a ligand exchange reaction between phenyliodine diacetate and excess carboxylic acid. Another methodology used an oxidation reaction between iodobenzene and excess carboxylic acid. The purpose of making the phenyliodine dicarboxylate compounds was to test their solubility and investigate if Hypervalent Iodine-Guided Electrophilic Substitution (HIGES) reactions are possible in nonpolar solvents such as hexane, diethyl ether, and toluene. The oxidation reaction provided a lower yield, but a higher level of purity which is important for accurate assessment of the synthesized compounds’ solubility. Phenyliodine dicarboxylate moieties of butanoate, adamantanoate, decanoate, trifluoroacetic acid, 2-ethylhexanoate, 2-ethylpentanoate, and 2-methylpentanoate were synthesized with the latter three compounds representing a novel class of liquid-state phenyliodine dicarboxylates. The liquid phenyl iodine dicarboxylate compounds have the potential to be used in industrial chemistry to inject into reactions without the need of solvent. Computational chemistry was used to explore the potential rotamers and diastereomers of the relevant synthesized phenyliodine dicarboxylates.

Synthesis and solubility of aliphatic phenyliodine dicarboxylates

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