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

Smonou, I./ Khan, S./ Foote, C. S./ Elemes, Y./ Mavridis, I. M./ Pantidou, A./ Orfanopoulos, M.


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.
Institution and School/Department of submitter: Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
Keywords: triazolinedione-olefin reactions,singlet oxygen,ene-reaction,photo-oxidation,low-temperature,chemistry,mechanism,n-phenyl-1,2,4-triazoline-3,5-dione,dependence,indenes
URI: http://olympias.lib.uoi.gr/jspui/handle/123456789/9028
ISSN: 0002-7863
Link: <Go to ISI>://A1995RJ03500006
http://pubs.acs.org/doi/pdfplus/10.1021/ja00132a006
Publisher: American Chemical Society
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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