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Alkynes to Reactive Intermediates vi...

Xu, Qian,

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Alkynes to Reactive Intermediates via Cycloaddition Reactions: Structure, Reactivity, and Mechanism /

Record Type:	Electronic resources : Monograph/item
Title/Author:	Alkynes to Reactive Intermediates via Cycloaddition Reactions: Structure, Reactivity, and Mechanism // Qian Xu.
Author:	Xu, Qian,
Description:	1 electronic resource (450 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 86-03, Section: B.
Contained By:	Dissertations Abstracts International86-03B.
Subject:	Chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30992191
ISBN:	9798384097662

Alkynes to Reactive Intermediates via Cycloaddition Reactions: Structure, Reactivity, and Mechanism /
Xu, Qian,

Alkynes to Reactive Intermediates via Cycloaddition Reactions: Structure, Reactivity, and Mechanism /Qian Xu. - 1 electronic resource (450 pages)

Source: Dissertations Abstracts International, Volume: 86-03, Section: B.

Reactive intermediates are highly reactive molecules featured by having short lifetimes. Their generations, structures, and reactivities are essential to the field of chemistry and have been attracting increasing attention. More often than not, the generation of a reactive intermediate invokes the use of catalysts, reagents, additives or irradiation. Direct generation of reactive intermediates under thermal, uncatalyzed, reagent- additive-free conditions remains a less explored but attractive strategy. The simple and straightforward setup of thermal reactions make it cost-efficient, reproducible, scalable, and practical for synthesis. More importantly, it also provides a platform for the discovery of novel reactivities and enables the construction of complex molecules. An alkyne is a particularly interesting functional group that can be further converted into reactive intermediates. On the one hand, alkynes generally have ample kinetic stability to render them easy to prepare, easy to handle, and shelf-stability that makes many of them commercially available. On the other, alkynes have inherently weak pi-bonds that can provide considerable favorable enthalpic contribution when they participate in a transformation, which can be a pivotal thermodynamic driving force for a thermal reaction. Furthermore, the high degree of unsaturation of an alkyne confers versatile modes of reactivities between alkynes and their reaction partners. These features synergistically make alkynes ideal precursors to reactive intermediates. Yet there remains a gap between alkynes and reactive intermediates, cycloaddition reactions provide a potential bridge for commuting. In this document, I will demonstrate how thermal, additive-free cycloaddition approaches convert alkynes into reactive intermediates including: i) strained reactive intermediates such as benzynes, 1,2,4-cyclohexatrienes, and 6-aza-1,2,4-cylcohexatrienes; ii) bond-deficient reactive intermediates such, a,3-dehydrotoluenes (DHTs), and free carbenes. DFT computations have provided crucial guidance for the reaction design and revealed valuable mechanistic insights across my entire research.

English

ISBN: 9798384097662Subjects--Topical Terms:

516420
Chemistry.
Subjects--Index Terms:

Cycloaddition reactions

Alkynes to Reactive Intermediates via Cycloaddition Reactions: Structure, Reactivity, and Mechanism /
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245 1 0 $a Alkynes to Reactive Intermediates via Cycloaddition Reactions: Structure, Reactivity, and Mechanism / $c Qian Xu.
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500 $a Source: Dissertations Abstracts International, Volume: 86-03, Section: B.
500 $a Advisors: Hoye, Thomas R. Committee members: Distefano, Mark; Harki, Daniel; Roberts, Courtney.
502 $b Ph.D. $c University of Minnesota $d 2024.
520 $a Reactive intermediates are highly reactive molecules featured by having short lifetimes. Their generations, structures, and reactivities are essential to the field of chemistry and have been attracting increasing attention. More often than not, the generation of a reactive intermediate invokes the use of catalysts, reagents, additives or irradiation. Direct generation of reactive intermediates under thermal, uncatalyzed, reagent- additive-free conditions remains a less explored but attractive strategy. The simple and straightforward setup of thermal reactions make it cost-efficient, reproducible, scalable, and practical for synthesis. More importantly, it also provides a platform for the discovery of novel reactivities and enables the construction of complex molecules. An alkyne is a particularly interesting functional group that can be further converted into reactive intermediates. On the one hand, alkynes generally have ample kinetic stability to render them easy to prepare, easy to handle, and shelf-stability that makes many of them commercially available. On the other, alkynes have inherently weak pi-bonds that can provide considerable favorable enthalpic contribution when they participate in a transformation, which can be a pivotal thermodynamic driving force for a thermal reaction. Furthermore, the high degree of unsaturation of an alkyne confers versatile modes of reactivities between alkynes and their reaction partners. These features synergistically make alkynes ideal precursors to reactive intermediates. Yet there remains a gap between alkynes and reactive intermediates, cycloaddition reactions provide a potential bridge for commuting. In this document, I will demonstrate how thermal, additive-free cycloaddition approaches convert alkynes into reactive intermediates including: i) strained reactive intermediates such as benzynes, 1,2,4-cyclohexatrienes, and 6-aza-1,2,4-cylcohexatrienes; ii) bond-deficient reactive intermediates such, a,3-dehydrotoluenes (DHTs), and free carbenes. DFT computations have provided crucial guidance for the reaction design and revealed valuable mechanistic insights across my entire research.
546 $a English
590 $a School code: 0130
650 4 $a Chemistry. $3 516420
650 4 $a Thermodynamics. $3 517304
650 4 $a Analytical chemistry. $3 3168300
650 4 $a Organic chemistry. $3 523952
653 $a Cycloaddition reactions
653 $a Alkynes
653 $a Reactive intermediates
653 $a Thermal reaction
653 $a Carbene
690 $a 0485
690 $a 0486
690 $a 0348
690 $a 0490
710 2 $a University of Minnesota. $b Chemistry. $e degree granting institution. $3 3820961
720 1 $a Hoye, Thomas R. $e degree supervisor.
773 0 $t Dissertations Abstracts International $g 86-03B.
790 $a 0130
791 $a Ph.D.
792 $a 2024
856 4 0 $u https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30992191