Reaction of a triazolinedione with simple alkenes. Isolation and characterization of hydration products

The reaction of N-phenyltriazolinedione with three simple alkyl-substituted alkenes in water/alcohol or water/acetone solution was found to give a mixture of the corresponding ene and water addition products. The new hydration products were characterized by spectroscopy, and in one case, also by X-ray diffraction analysis. Thermodynamic parameters were determined for the reactions involving 2-methylbut-2-ene, TriME, and 2,3-dimethylbut-2-ene, TetraMe, in accordance with an ‘SN2-like’, nucleophilic attack on a closed aziridinium imide (AI) intermediate by water.

Graphical abstractThe reaction of N-phenyltriazolinedione with simple alkenes in alcohol/water mixtures affords, in addition to the ene adduct, an alcohol which arises from the addition of water to the aziridinium imide intermediate. The structures of the new hydration products have been established by X-ray analysis and spectroscopy.Figure optionsDownload full-size imageDownload as PowerPoint slide