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The Stereoselectivity of Mediated El...

Willson, Laurel Rae.

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The Stereoselectivity of Mediated Electrohydrocyclization Reactions Using a Chiral Nickel (II) Salen Catalyst.

Record Type:	Electronic resources : Monograph/item
Title/Author:	The Stereoselectivity of Mediated Electrohydrocyclization Reactions Using a Chiral Nickel (II) Salen Catalyst./
Author:	Willson, Laurel Rae.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2023,
Description:	119 p.
Notes:	Source: Masters Abstracts International, Volume: 85-05.
Contained By:	Masters Abstracts International85-05.
Subject:	Chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30632703
ISBN:	9798380850360

The Stereoselectivity of Mediated Electrohydrocyclization Reactions Using a Chiral Nickel (II) Salen Catalyst.
Willson, Laurel Rae.

The Stereoselectivity of Mediated Electrohydrocyclization Reactions Using a Chiral Nickel (II) Salen Catalyst. - Ann Arbor : ProQuest Dissertations & Theses, 2023 - 119 p.

Source: Masters Abstracts International, Volume: 85-05.

Thesis (M.S.)--California State University, Sacramento, 2023.

This item must not be sold to any third party vendors.

Organic electrochemistry has become a favorable form of chemical synthesis in recent years due to the ability of these being more environmentally friendly methods. Electrochemical methods generally require a smaller amount of solvent used, decreasing toxic waste produced in synthesis reactions. Organic electrochemistry allows for selective introduction or removal of electrons from a functional group, reversing the functional group's polarity. The polarity reversal of a functional group allows for electroreductive cyclization reactions and electrohydrocyclization reactions to occur. Baizer first successfully performed electrohydrocyclization reactions via a direct pathway in 1966. Little studied electroreductive cyclization reactions of aldehydes and ketones via a direct pathway in 1988. In 2005 Miranda and Little found that the introduction of a metal-salen mediator (catalyst) in the electroreductive cyclization reactions and electrohydrocyclization reactions would increase the rate of the reaction and the product yield. Products of electroreductive cyclization reactions and electrohydrocyclization reactions have been shown to favor the trans stereoisomer of the cyclized electroreductive cyclization and electrohydrocyclization product over the cis stereoisomer. Computational chemistry has shown{A0}that if a chiral mediator, catalyst, is employed in an electroreductive cyclization reaction or an electrohydrocyclization reaction under kinetic conditions, the cis stereoisomer can be favored instead of the trans stereoisomer. The following thesis examines the effects of a chiral metal salen mediator on electrohydrocyclization reactions under kinetic conditions. The electrohydrocyclization reactions were performed at five different reaction temperatures from room temperature to as low as 5 {phono}{mllhring}C to examine the effects lowering the temperature will have on the stereochemistry of the product. The cis stereoisomer of the product was favored for the two reactions with temperatures above 15 {phono}{mllhring}C and the trans stereoisomer was favored in the three reactions with temperatures at 15 {phono}{mllhring}C and below.

ISBN: 9798380850360Subjects--Topical Terms:

516420
Chemistry.
Subjects--Index Terms:

Electrohydrocyclization reactions

The Stereoselectivity of Mediated Electrohydrocyclization Reactions Using a Chiral Nickel (II) Salen Catalyst.
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500 $a Source: Masters Abstracts International, Volume: 85-05.
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520 $a Organic electrochemistry has become a favorable form of chemical synthesis in recent years due to the ability of these being more environmentally friendly methods. Electrochemical methods generally require a smaller amount of solvent used, decreasing toxic waste produced in synthesis reactions. Organic electrochemistry allows for selective introduction or removal of electrons from a functional group, reversing the functional group's polarity. The polarity reversal of a functional group allows for electroreductive cyclization reactions and electrohydrocyclization reactions to occur. Baizer first successfully performed electrohydrocyclization reactions via a direct pathway in 1966. Little studied electroreductive cyclization reactions of aldehydes and ketones via a direct pathway in 1988. In 2005 Miranda and Little found that the introduction of a metal-salen mediator (catalyst) in the electroreductive cyclization reactions and electrohydrocyclization reactions would increase the rate of the reaction and the product yield. Products of electroreductive cyclization reactions and electrohydrocyclization reactions have been shown to favor the trans stereoisomer of the cyclized electroreductive cyclization and electrohydrocyclization product over the cis stereoisomer. Computational chemistry has shown{A0}that if a chiral mediator, catalyst, is employed in an electroreductive cyclization reaction or an electrohydrocyclization reaction under kinetic conditions, the cis stereoisomer can be favored instead of the trans stereoisomer. The following thesis examines the effects of a chiral metal salen mediator on electrohydrocyclization reactions under kinetic conditions. The electrohydrocyclization reactions were performed at five different reaction temperatures from room temperature to as low as 5 {phono}{mllhring}C to examine the effects lowering the temperature will have on the stereochemistry of the product. The cis stereoisomer of the product was favored for the two reactions with temperatures above 15 {phono}{mllhring}C and the trans stereoisomer was favored in the three reactions with temperatures at 15 {phono}{mllhring}C and below.
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