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Electrophilic Cyanation of Alkenyl T...

Graham, Joshua Morgan,

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Electrophilic Cyanation of Alkenyl Tosylates, Ketones and Amines Using Disubstituted Malononitriles /

Record Type:	Electronic resources : Monograph/item
Title/Author:	Electrophilic Cyanation of Alkenyl Tosylates, Ketones and Amines Using Disubstituted Malononitriles // Joshua Morgan Graham.
Author:	Graham, Joshua Morgan,
Description:	1 electronic resource (348 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 86-10, Section: B.
Contained By:	Dissertations Abstracts International86-10B.
Subject:	Organic chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=31764759
ISBN:	9798310392014

Electrophilic Cyanation of Alkenyl Tosylates, Ketones and Amines Using Disubstituted Malononitriles /
Graham, Joshua Morgan,

Electrophilic Cyanation of Alkenyl Tosylates, Ketones and Amines Using Disubstituted Malononitriles /Joshua Morgan Graham. - 1 electronic resource (348 pages)

Source: Dissertations Abstracts International, Volume: 86-10, Section: B.

This thesis describes new methods for the synthesis of alkenyl nitriles, β-ketonitriles, and cyanamides using various disubstituted malononitriles as electrophilic cyanation reagents. These approaches may be of interest to workers attempting to access compounds of those types.Chapter 1 provides a brief overview of the thesis topics and compares nucleophilic to electrophilic cyanation.Chapter 2 describes a novel method for the construction of alkenyl nitriles from alkenyl tosylates using disubstituted malononitriles as electrophilic cyanating reagents under reductive nickel catalysis.Chapter 3 describes a novel method for the synthesis of β-ketonitriles from ketones and disubstituted malononitriles under basic conditions. Several β-ketoenamines were found to be produced using similar conditions, and their synthesis is also elaborated.Chapter 4 describes continued efforts related to the synthesis cyanamides using disubstituted malononitriles under basic conditions. A novel ortho-functionalization of the cyanating reagent byproduct was observed during reaction optimization.

English

ISBN: 9798310392014Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

Electrophilic cyanation

Electrophilic Cyanation of Alkenyl Tosylates, Ketones and Amines Using Disubstituted Malononitriles /
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245 1 0 $a Electrophilic Cyanation of Alkenyl Tosylates, Ketones and Amines Using Disubstituted Malononitriles / $c Joshua Morgan Graham.
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300 $a 1 electronic resource (348 pages)
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500 $a Source: Dissertations Abstracts International, Volume: 86-10, Section: B.
500 $a Advisors: Rousseaux, Sophie Committee members: Lautens, Mark; Taylor, Mark.
502 $b Ph.D. $c University of Toronto (Canada) $d 2025.
520 $a This thesis describes new methods for the synthesis of alkenyl nitriles, β-ketonitriles, and cyanamides using various disubstituted malononitriles as electrophilic cyanation reagents. These approaches may be of interest to workers attempting to access compounds of those types.Chapter 1 provides a brief overview of the thesis topics and compares nucleophilic to electrophilic cyanation.Chapter 2 describes a novel method for the construction of alkenyl nitriles from alkenyl tosylates using disubstituted malononitriles as electrophilic cyanating reagents under reductive nickel catalysis.Chapter 3 describes a novel method for the synthesis of β-ketonitriles from ketones and disubstituted malononitriles under basic conditions. Several β-ketoenamines were found to be produced using similar conditions, and their synthesis is also elaborated.Chapter 4 describes continued efforts related to the synthesis cyanamides using disubstituted malononitriles under basic conditions. A novel ortho-functionalization of the cyanating reagent byproduct was observed during reaction optimization.
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650 4 $a Physical chemistry. $3 1981412
650 4 $a Analytical chemistry. $3 3168300
653 $a Electrophilic cyanation
653 $a Malononitriles
653 $a Alkenyl nitriles
653 $a Amines
653 $a Alkenyl tosylates
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710 2 $a University of Toronto (Canada). $b Chemistry. $e degree granting institution. $3 3816061
720 1 $a Rousseaux, Sophie $e degree supervisor.
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791 $a Ph.D.
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