Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection

Permanent URI for this collectionhttps://hdl.handle.net/11147/7148

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Subject: search.filters.subject.Regioselectivity

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  • Article
    Citation - WoS: 7
    Citation - Scopus: 7
    Regio- and Stereo-Chemical Ring-Opening Reactions of the 2,3-Epoxy Alcohol Derivative With Nucleophiles: Explanation of the Structures and C-2 Selectivity Supported by Theoretical Computations
    (Elsevier, 2022) Gündoğdu, Özlem; Şanlı Mohamed, Gülşah; Çelebioğlu, Neslihan; Anıl, Barış; Şahin, Ertan; Şanlı Mohamed, Gülşah; Bozkaya, Uğur; Kara, Yunus; 04.01. Department of Chemistry; 04. Faculty of Science; 01. Izmir Institute of Technology
    The ring-opening reactions of (1aS,2S,6bR)-5-ethyl-2-hydroxyhexahydro-4H-oxireno[2,3-e]isoindole-4,6(5H)-dione were investigated under very mild and nonchelated conditions. C-2 selective ring-opening products were obtained with nucleophilic additions such as Cl−, Br− and N3−. The exact configuration of (3aS,4R,5R,6S,7aS)-5-chloro-2-ethyl-4,6-dihydroxyhexahydro-1H-isoindole-1,3(2H)-dione was determined by X-Ray diffraction analysis which was obtained from the reaction of epoxy alcohol with HCl. On the other hand, theoretical computations were carried out to explain the regioselectivity in the ring opening reaction of epoxy alcohols. The results showed that the ring-opening reaction of both epoxy alcohols proceeds in a kinetically controlled manner and regioselectivity occurs depending on the transition state.
  • Article
    Citation - WoS: 9
    Citation - Scopus: 10
    Iron-Promoted 1,5-Substitution (sn2' Reactions of Enyne Acetates and Oxiranes With Grignard Reagents
    (Wiley, 2017) Taç, Doğan; Aytaç, İsmet Arınç; Artok, Levent; Kuş, Melih; Ziyanak, Fırat; Kuş, Melih; Ziyanak, Fırat; 04.01. Department of Chemistry; 04. Faculty of Science; 01. Izmir Institute of Technology
    Acetate derivatives of 2-en-4-yne alcohols 1 and enyne oxiranes 4 regioselectively underwent 1,5-substitution (SN2′′) reactions with Grignard reagents in the presence of an iron compound to provide vinylallenes exclusively with the (E)-configuration. An alkali salt was needed to avoid the hydride-promoted reductive 1,5-substitution pathway for 1, whereas no such additive was needed for the effective conversion of 4 into the desired alkylated or arylated vinylallene structure.