Reaction of a triazolinedione with simple alkenes. Isolation and characterization of hydration products (Journal article)

Syrgiannis, Z./ Koutsianopoulos, F./ Muir, K. W./ Elemes, Y.


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.
Institution and School/Department of submitter: Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
Keywords: ene reactions,triazolinediones,solvent addition,water addition,thermodynamic parameters,x-ray,ene reaction,n-phenyltriazolinedione,singlet oxygen,benzyltriphenylphosphonium peroxymonosulfate,thiols,disulfides,oxidation,solvent,mechanism,efficient
URI: http://olympias.lib.uoi.gr/jspui/handle/123456789/9022
ISSN: 0040-4039
Link: <Go to ISI>://000263152800007
http://ac.els-cdn.com/S0040403908020601/1-s2.0-S0040403908020601-main.pdf?_tid=f6cacca45afcda900d6ec87b257ff93f&acdnat=1333029130_9fb5da02b79327d3630a6785f23ebdb5
Publisher: Elsevier
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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