73971-01-4Relevant academic research and scientific papers
Solvent Effect in Pericyclic Reactions. IX. The Ene Reaction.
Desimoni, G.,Faita, G.,Righetti, P. P.,Sfulcini, A.,Tsyganov, D.
, p. 1821 - 1832 (1994)
The solvent effect on the ene reactions of diethylazodicarboxylate and triazolindione was determined in 18 and 16 solvents respectively.The first enophile gives a solvent effect that depends on solvent acidity (type a solvent effect), while in the second
Reaction of a triazolinedione with simple alkenes. Isolation and characterization of hydration products
Syrgiannis, Zois,Koutsianopoulos, Fotios,Muir, Kenneth W.,Elemes, Yiannis
body text, p. 277 - 280 (2009/04/11)
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
Isotope effects and the mechanism of triazolinedione ene reactions. Aziridinium imides are innocent bystanders
Singleton, Daniel A.,Hang, Chao
, p. 11885 - 11893 (2007/10/03)
Kinetic isotope effects were determined for the ene reactions of 4-phenyl-1,2,4-triazoline-2,5-dione with 2-methyl-2-butene and 2-methyl-1-pentene. In each case highly inverse (kH/kD = 0.87-0.88) vinylic deuterium isotope effects were observed. Large 13C isotope effects were observed for the less-substituted olefinic carbons of each alkene and much smaller effects were found in the more-substituted olefinic carbon. Becke3LYP calculations of the mechanistic pathway for the ene reaction of 1,2,4-triazoline-2,5-dione with isobutene, 2-methyl-2-butene, and tetramethylethylene predict a new mechanism for these reactions involving an open biradical as the key intermediate. This biradical may either form the ene product or reversibly form an intermediate aziridinium imide. The validity of these calculations is supported by a comparison of experimental and theoretically predicted isotope effects. A curved Arrhenius plot of product ratios was found for the ene reaction of 2-methyl-1-pentene in the presence of methanol. This is inconsistent with a simple two-step ene mechanism involving only an aziridinium imide intermediate, but the curvature of this plot could be modeled well by the theoretical mechanism using enthalpy and entropy parameters close to theoretically predicted values. A variety of observations associated with these reactions are examined and found to support the new mechanism.
Ene Reaction of Triazolinediones with Alkenes. 1. Structure and Properties of Products
Ohashi, Shinichi,Leong, Koon-wah,Matyjaszewski, Kristoff,Butler, George B.
, p. 3467 - 3471 (2007/10/02)
The structures of ene products from reaction of triazolinediones with alkenes and polyisoprene were studied by using (1)H NMR.The pKa values of the ene products were measured.The reactivity and stability of the ene products were also studied.
