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003 OCoLC;

005 20200504094335.0;

006 m o d ;

007 cr unu||||||||;

008 200313s2019 ncua obm 000 0 eng d;

035 a| (Sirsi) o1144494873;

035 a| (OCoLC)1144494873;

049 a| EREE;

090 a| QD262;

100 1 a| Javed, Erman,e| author.?| UNAUTHORIZED;

245 10 a| Platinum catalyzed synthesis of alpha-ketoester via C-H functionalization /c| by Erman Javed.;

264 1 a| [Greenville, N.C.] :b| [East Carolina University],c| 2019.;

300 a| 76 pages :b| illustrations;

336 a| textb| txt2| rdacontent;

337 a| computerb| c2| rdamedia;

338 a| online resourceb| cr2| rdacarrier;

347 a| text fileb| PDFc| 1.74 MB2| rda;

538 a| System requirements: Adobe Reader.;

538 a| Mode of access: World Wide Web.;

502 b| M.S.c| East Carolina Universityd| 2019.;

500 a| Presented to the faculty of the Department of Chemistry;

500 a| Advisor: Shouquan Huo;

500 a| Title from PDF t.p. (viewed April 27, 2020).;

520 3 a| Alpha-ketoesters have proven to be useful in a variety of fields. They have found wide spread applications in pharmaceuticals, photochemistry, and biology. Additionally, they are of great interest in synthetic chemistry and are frequently used as a precursor to many useful organic compounds including alpha-keto acids, alpha-hydroxy acids, and alpha-amino acids. Numerous methods have been reported for synthesizing alpha-ketoesters but they all amount to a few notable drawbacks. Herein reported is a potentially more effective transition metal catalyzed reaction to synthesize alpha-ketoester via C-H functionalization. A series of ligands with structural modifications have been designed, synthesized and acylated to shed light on the scope and limitations of the reaction. An inexpensive and readily accessible reagent namely ethyl chlorooxoacetate was employed as the acylating reagent. Reaction conditions were optimized by screening various solvents and catalysts. A variety of solvents were found useful in this reaction, including chlorobenzene, benzonitrile, toluene, and m-xylene although the best results were obtained when chlorobenzene was used. The reaction showed great tolerance to both electron withdrawing and donating groups on the phenyl ring however some electronic effects were observed and it was found that the presence of electron withdrawing group on the phenyl ring decelerated the acylation reaction. Experimental results of the acylation reaction will be reported and the mechanistic implications of these results will be discussed.;

504 a| Includes bibliographical references.;

650 0 a| Organic compoundsx| Synthesis.=| ^A1214;

650 0 a| Ketonic acids.=| ^A1407323;

650 0 a| Chemistry, Organic.=| ^A458360;

653 a| alpha-ketoester;

653 a| C-H Functionalization;

700 1 a| Huo, Shouquan,e| degree supervisor.?| UNAUTHORIZED;

710 2 a| East Carolina University.b| Department of Chemistry.?| UNAUTHORIZED;

856 40 z| Access via ScholarShipu| http://hdl.handle.net/10342/7652;

949 o| wjh;

994 a| C0b| ERE;

596 a| 1 4;

998 a| 5266624;

999 a| CLICK ON WEB ADDRESSw| ASISc| 1i| 5266624-1001l| JNETm| JOYNERr| Ys| Yt| JNE3ETDu| 3/13/2020x| ETDz| JERESOURCE;

999 a| CLICK ON WEB ADDRESSw| ASISc| 1i| 5266624-2001l| HSLELECm| HSLr| Ys| Yt| HEETDu| 3/13/2020x| ETDz| HERESOURCE;

Platinum catalyzed synthesis of alpha-ketoester via C-H functionalization / by Erman Javed.

Author/creator	Javed, Erman author.
Other author	Huo, Shouquan, degree supervisor.
Other author	East Carolina University. Department of Chemistry.
Format	Theses and dissertations
Publication	[Greenville, N.C.] : [East Carolina University], 2019.
Description	76 pages : illustrations
Supplemental Content	Access via ScholarShip
Subjects	Organic compounds--Synthesis. Ketonic acids. Chemistry, Organic.

Summary	Alpha-ketoesters have proven to be useful in a variety of fields. They have found wide spread applications in pharmaceuticals, photochemistry, and biology. Additionally, they are of great interest in synthetic chemistry and are frequently used as a precursor to many useful organic compounds including alpha-keto acids, alpha-hydroxy acids, and alpha-amino acids. Numerous methods have been reported for synthesizing alpha-ketoesters but they all amount to a few notable drawbacks. Herein reported is a potentially more effective transition metal catalyzed reaction to synthesize alpha-ketoester via C-H functionalization. A series of ligands with structural modifications have been designed, synthesized and acylated to shed light on the scope and limitations of the reaction. An inexpensive and readily accessible reagent namely ethyl chlorooxoacetate was employed as the acylating reagent. Reaction conditions were optimized by screening various solvents and catalysts. A variety of solvents were found useful in this reaction, including chlorobenzene, benzonitrile, toluene, and m-xylene although the best results were obtained when chlorobenzene was used. The reaction showed great tolerance to both electron withdrawing and donating groups on the phenyl ring however some electronic effects were observed and it was found that the presence of electron withdrawing group on the phenyl ring decelerated the acylation reaction. Experimental results of the acylation reaction will be reported and the mechanistic implications of these results will be discussed.
General note	Presented to the faculty of the Department of Chemistry
General note	Advisor: Shouquan Huo
General note	Title from PDF t.p. (viewed April 27, 2020).
Dissertation note	M.S. East Carolina University 2019.
Bibliography note	Includes bibliographical references.
Technical details	System requirements: Adobe Reader.
Technical details	Mode of access: World Wide Web.

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Platinum catalyzed synthesis of alpha-ketoester via C-H functionalization / by Erman Javed.

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