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 or 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 ‘S(N)2-like’, nucleophilic attack on a closed aziridinium imide (At) intermediate by water. (C) 2008 Elsevier Ltd. All rights reserved.