Please use this identifier to cite or link to this item: https://hdl.handle.net/11147/5700
Title: Coupling reactions of enyne oxiranes with Grignard reagents
Other Titles: Enin oksiranların Grignard reaktifleri ile kenetlenme tepkimeleri
Authors: Artok, Levent
Aytaç, İsmet Arınç
Keywords: Organic chemistry
Grignard reaction
Iron catalysis
Enyne oxiranes
Issue Date: Oct-2016
Publisher: Izmir Institute of Technology
Source: Aytaç, İ. A. (2016). Coupling reactions of enyne oxiranes with grignard reagents. Unpublished master's thesis, İzmir Institute of Technology, İzmir, Turkey
Abstract: Laboratory-synthesized (Z)-2,4-Enyne oxiranes were subjected iron-catalyzed reactions with Grignard reagents. The reactions afforded majorly E-configured vinylallenes with a hydroxyl group on the allylic carbon as the 1,5-(SN2'')-substitution products. However, in some case, along with the desired vinyllallenes products, 1,1- (SN2) and 1,3-substitution (SN2’) by-products were also recovered. Diastereo-selectivity of the method is strictly reliant on the syn/anti mode of the alkylation process. This study provides a new methodology for the synthesis of vinylallenes which are potential building blocks of biological active molecules.
Laboratuvarda sentezlenen (Z)-2,4-enin oksiran bileşiklerinin Grignard reaktifleri ile demir katalizli tepkimeleri gerçekleştirilmiştir. Bu tepkimeler ana ürün olarak 1,5-(SN2”)-sübstitüsyon ürünü olan E-konfigürasyona sahip allilik pozisyonunda hidroksil grubu bulunan vinilallen ürünleri vermektedir. 1,1-(SN2) ve 1,3-(SN2) ürünleri de bazı reaktiflerin tepkimelerinde oluşabilmektedir. Tepkimenin diastereo seçimliliği alkilasyonun yalnızca syn ya da anti modunda gerçekleşmesine bağlıdır. Bu çalışma, biyolojik olarak aktif moleküllerin çeşitli yapı taşları olabilecek vinylallen sentezi için yeni bir yöntem sunmaktadır.
Description: Thesis (Master)--İzmir Institute of Technology, Chemistry, İzmir, 2016
Includes bibliographical references (leaves: 68-73)
Text in English; Abstract: Turkish and English
xii, 195 leaves
URI: http://hdl.handle.net/11147/5700
Appears in Collections:Master Degree / Yüksek Lisans Tezleri

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