Reactions of Phenyltriazolinedione with Alkenes - Stereochemistry of Methanol Adducts to Aziridinium Imide Intermediates

 
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)
Reactions of Phenyltriazolinedione with Alkenes - Stereochemistry of Methanol Adducts to Aziridinium Imide Intermediates (EN)

Smonou, I. (EN)

Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας (EL)
Smonou, I. (EN)

The addition of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and the stereochemistry of methanol/PTAD adduct formation with cis- and trans-2-butenes, 1-methylcyclopentene, (E)-2-methyl-2-butene-1,1,1-d(3), and substituted indenes (indene, 2-methylindene, 2,3-dimethylindene) have been investigated. There is no loss of stereochemistry in the addition of MeOH and PTAD to butenes, 1-methylcyclopentene, 2-methyl-2-butene, and indene. However, in methyl-substituted indenes 9 and 14, loss of stereochemistry at the reaction center is observed. An aziridinium imide (AI) is proposed as an intermediate in all these systems. The stability of the AI intermediate and its equilibration with an open zwitterion depend on the particular system. Only in the benzylically-stabilized tertiary indenes is the open zwitterion stable enough to cause loss of stereochemistry. (EN)

triazolinedione-olefin reactions (EN)

Πανεπιστήμιο Ιωαννίνων (EL)
University of Ioannina (EN)

J Am Chem Soc (EN)

English

1995

<Go to ISI>://A1995RJ03500006

American Chemical Society (EN)



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