Thermal reaction of ethynylphthalimides and hydration of N-(4-ethynylphenyl)phthalimide

Three ethynyl substituted phenylphthalimides were prepared and characterized by high pressure liquid chromatography, differential scanning calorimetry, and mass spectroscopy. When the preparation of N-(4-ethynylphenyl)phthalimide was attempted by the thermal cyclodehydration of N-(4-ethynylphenyl)-2-carboxybenzamide, N-(4-acetylphenyl)phthalimide was obtained as the major component. This unusual hydration of an ethynyl group was investigated and a mechanism was proposed to explain it.