An interplay in the regioselectivity induced by non bonding interactions, in the ene reactions of singlet oxygen and triazolinediones with tetrasubstituted alkenes
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Authors
Elemes, Y.
Stratakis, M.
Orfanopoulos, M.
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Elsevier
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peer reviewed
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Tetrahedron Lett
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The ene reactions of N-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and singlet oxygen (O-1(2)) with tetrasubstituted alkenes, follow regioselectivity trends governed mainly by 1,3-non bonded interactions (type I) for the case of PTAD, and mainly by the steric hindrance caused during the formation of the new double bond (type II) for the case of O-1(2). The results are explained hi terms of a ''late'' product forming transition state of hydrogen abstraction for triazolinediones and an ''early'' transition st;lte for the analogous singlet oxygen reaction. (C) 1997 Elsevier Science Ltd.
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geminal selectivity, aziridinium imide, olefin reactions, cis-alkenes, mechanism
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<Go to ISI>://A1997XU80200036
http://ac.els-cdn.com/S0040403997014718/1-s2.0-S0040403997014718-main.pdf?_tid=f9af069958584eb0aa0f87553be881bb&acdnat=1333029082_fa2d0031985121b5f7b17590cd422322
http://ac.els-cdn.com/S0040403997014718/1-s2.0-S0040403997014718-main.pdf?_tid=f9af069958584eb0aa0f87553be881bb&acdnat=1333029082_fa2d0031985121b5f7b17590cd422322
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en
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Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας