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

โœ Scribed by Zois Syrgiannis; Fotios Koutsianopoulos; Kenneth W. Muir; Yiannis Elemes

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
182 KB
Volume
50
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

a b s t r a c t

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 'S N 2-like', nucleophilic attack on a closed aziridinium imide (AI) intermediate by water.

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