Reaction of N-Substituted 1,2,4-Triazoline-3,5-Diones and Trans-Cyclooctene - Direct Observation of an Aziridinium Imide

 
This item is provided by the institution :
University of Ioannina
Repository :
Repository of UOI Olympias
see the original item page
in the repository's web site and access all digital files if the item*
share



1995 (EN)
Reaction of N-Substituted 1,2,4-Triazoline-3,5-Diones and Trans-Cyclooctene - Direct Observation of an Aziridinium Imide (EN)

Poon, T. H. W. (EN)

Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας (EL)
Poon, T. H. W. (EN)

4-R-1,2,4-triazoline-3,5-diones (R = Me (MTAD), R = Ph (PTAD)) react stereospecifically with transcyclooctene (1) to give addition products 2, 3, and 4. The products of the reaction and those obtained from nucleophilic trapping of the intermediate with methanol and water suggest an aziridinium imide followed by an open cation that can lead to transannular ring closure and hydride shifts. At -83 degrees C a trans-aziridinium imide intermediate is formed nearly quantitatively and can be directly observed via NMR spectroscopy. An activation energy of 16.2 kcal/mol was measured for the decomposition of the aziridinium imide. A mechanism is proposed for the reaction. (EN)

triazolinedione-olefin reactions (EN)

Πανεπιστήμιο Ιωαννίνων (EL)
University of Ioannina (EN)

J Am Chem Soc (EN)

English

1995

<Go to ISI>://A1995TC32600008

American Chemical Society (EN)



*Institutions are responsible for keeping their URLs functional (digital file, item page in repository site)