Synthesis, structure, and reactivity of 2,6-diaryl-4-hydroxybenzenethiol

Novel 2,6-diaryl-4-hydroxybenzenethiol, 2,6-bis(2,4,6-triisopropylphenyl)-4-hydroxybenzenethiol, was synthesized from the corresponding 2,6-diaryl-4-bromoiodobenzene as a potential precursor of the corresponding thiobenzoquinone. The X-ray crystallography showed that the two aryl groups are nearly orthogonal to the central benzene ring and shield the mercapto group, but there still remains open space and the oxidation of the 4-hydroxybenzenethiol by MnO₂ led to the formation of the corresponding disulfide. The oxidation of the 4-hydroxybenzenethiol as well as the corresponding disulfide was studied, and the spectroscopic studies suggested the formation of the labile thiobenzoquinone.