Synthesis of tempo containing chiral polymers for kinetic resolution of secondary alcohols.

Download

index.pdf

Date

2020

Author

Yücel, Ece Ayç

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

344
views

145
downloads

Optically pure secondary alcohols are important building blocks for the synthesis of chemicals used in pharmaceutical sciences. Kinetic resolution of secondary alcohols through selective oxidation of one enantiomer to the corresponding ketone is a classical and efficient method to obtain enantiopure alcohols. An oxidative kinetic resolution is achieved by exploiting two enantiomers’ unequal rates of oxidation reaction with a chiral reagent or catalyst. The general approach towards a kinetic resolution via alcohol oxidation utilizes nitroxyl radicals on a chiral environment. The oxidations with these radicals are highly efficient catalytic oxidations due to fast and efficient turnover and the use of inexpensive oxidants. In this study, 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) containing chiral polymers were synthesized via ring opening metathesis polymerization. Afterwards, the synthesized polymers were used as catalysts for the oxidative kinetic resolution of 1-phenyl ethanol. Morever, a TEMPO containing polymer was employed as a cathode material in the construction of a organic radical battery.

Subject Keywords

Oxidation., Keywords: Oxidation, Kinetic Resolution, TEMPO Radical.

URI

http://etd.lib.metu.edu.tr/upload/12625190/index.pdf
https://hdl.handle.net/11511/45437

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Preparation of lead zirconate titanate (Pb(Zr0.52Ti0.48)O-3) by homogeneous precipitation and calcination Oren, EE; Tas, AC (1998-05-06) Aqueous solutions of lead chloride (PbCl2), zirconium oxychloride (ZrOCl2.8H(2)O) and titanium tetrachloride (TiCl4), in appropriate volumetric amounts, were used as the starting materials in the synthesis of phase-pure Pb(Zr0.52Ti0.48)O-3 powders. Preparation of the phase-pure PZT powders were achieved, in the presence of urea (CH4N2O), by the chemical powder synthesis route of homogeneous precipitation.
Synthesis and optimization of tempo based polymeric oxidation catalysts Tosun, Ayşegül; Tanyeli, Cihangir; Department of Chemistry (2002) ree nitroxyl radicals are popular in alcohol oxidation reactions as catalysts. The most useful ones are TEMPO (2,2,6,6-tetramethylpiperidinoxyl) derivatives. In this thesis, TEMPO based polymeric catalyst systems were synthesized. The most important property of these catalysts are being homogeneous and recyclable systems. In the synthetic strategy, the monomer systems which are needed for polymerization were synthesized from easily available norbornene derivatives via Mukaiyama and DCC coupling reactions. T...
Synthesis of polymer-supported TEMPO catalysts and their application in the oxidation of various alcohols Tanyeli, Cihangir (2003-02-17) We describe the synthesis of a recyclable polymer-supported TEMPO as a catalyst in the Anelli oxidation of various primary alcohols to afford the corresponding aldehydes in good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
Electrochemical and chemical oxidation of K(C2H5OCS2),[Ni(C2H5OCS2)(2)] and [N(C2H5)(4)][Ni(C2H5OCS2)(3)] Dag, O; Önal, Ahmet Muhtar; Isci, H (1996-06-26) Electrochemical and chemical oxidation of (Et-Xan(-)), [Ni(Et-Xan)(2)] and [Ni(Et-Xan)(3)](-) (Et-Xan(-) = C2H5OCS2- have been studied by Cyclic Voltammetry and in situ UV-Vis spectroscopy in acetonitrile at room temperature. Cyclic Voltammograms (CV) of Et-Xan(-) and Ni(Et-Xan)(2) display one (0.00 V) and two (0.35 and 0.80 V) irreversible oxidation peaks, respectively, referenced to Ag/Ag+(0.10 M) electrode. However, CV of Ni(Et-Xan)(3)(-) displays one reversible (-0.15 V) and two irreversible (0.35, 0.80...
Synthesis of Functionalized Novel alpha-Amino-beta-alkoxyphosphonates through Regioselective Ring Opening of Aziridine-2-phosphonates Polat-Cakir, Sidika; Beksultanova, Nurzhan; Doğan, Özdemir (Wiley, 2019-11-01) Aziridines are highly useful compounds as building blocks for the synthesis of important organic compounds. Amino acid synthesis by aziridine ring opening reaction is a good example to the use of aziridines. Although this reaction is studied by many groups, the synthesis of amino phosphonic acids is less explored. In this study, we have carried out the ring opening reaction of aziridinyl phosphonates with a variety of alcohols including the more functional propargylic and allylic alcohols. These reactions p...

Citation Formats

E. A. Yücel, “Synthesis of tempo containing chiral polymers for kinetic resolution of secondary alcohols.,” Thesis (M.S.) -- Graduate School of Natural and Applied Sciences. Chemistry., Middle East Technical University, 2020.