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Reactivity of Seven-Membered-Ring tr...

Sanzone, Jillian Rose.

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Reactivity of Seven-Membered-Ring trans-Alkenes.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Reactivity of Seven-Membered-Ring trans-Alkenes./
Author:	Sanzone, Jillian Rose.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2018,
Description:	731 p.
Notes:	Source: Dissertation Abstracts International, Volume: 79-12(E), Section: B.
Contained By:	Dissertation Abstracts International79-12B(E).
Subject:	Chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10745144
ISBN:	9780438170452

Reactivity of Seven-Membered-Ring trans-Alkenes.
Sanzone, Jillian Rose.

Reactivity of Seven-Membered-Ring trans-Alkenes. - Ann Arbor : ProQuest Dissertations & Theses, 2018 - 731 p.

Source: Dissertation Abstracts International, Volume: 79-12(E), Section: B.

Thesis (Ph.D.)--New York University, 2018.

This dissertation describes the reactivity of seven-membered-ring trans-alkenes. In contrast to larger strained alkenes, few studies of trans-cycloheptenes exist because these compounds decompose at room temperature and are difficult to synthesize. Reactivity studies of trans-cycloheptenes are necessary for discovering new chemical reactivity and for using these highly reactive alkenes for applications in chemical biology and material science. A series of trans-oxasilacycloheptenes were synthesized to analyze how the different steric and electronic properties of these alkenes would affect reactivity. In addition to examining common transformations of strained alkenes, new reactions of alkenes were also discovered.

ISBN: 9780438170452Subjects--Topical Terms:

516420
Chemistry.

Reactivity of Seven-Membered-Ring trans-Alkenes.
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100 1 $a Sanzone, Jillian Rose. $3 3351345
245 1 0 $a Reactivity of Seven-Membered-Ring trans-Alkenes.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2018
300 $a 731 p.
500 $a Source: Dissertation Abstracts International, Volume: 79-12(E), Section: B.
500 $a Adviser: Keith A. Woerpel.
502 $a Thesis (Ph.D.)--New York University, 2018.
520 $a This dissertation describes the reactivity of seven-membered-ring trans-alkenes. In contrast to larger strained alkenes, few studies of trans-cycloheptenes exist because these compounds decompose at room temperature and are difficult to synthesize. Reactivity studies of trans-cycloheptenes are necessary for discovering new chemical reactivity and for using these highly reactive alkenes for applications in chemical biology and material science. A series of trans-oxasilacycloheptenes were synthesized to analyze how the different steric and electronic properties of these alkenes would affect reactivity. In addition to examining common transformations of strained alkenes, new reactions of alkenes were also discovered.
520 $a Several different transformations of seven-membered-ring trans -alkenes were explored. trans-Oxasilacycloheptenes were highly reactive in [4+2] cycloaddition reactions. Competition experiments showed that trans-cycloheptenes were more reactive in cycloaddition reactions than a trans-cyclooctene. trans-Oxasilacycloheptenes also reacted with a variety of electrophiles to form new products as single stereoisomers. Mechanistic studies indicated that the reactions of trans-alkenes with electrophiles proceeded through stepwise, zwitterionic mechanisms. Release of strain was not the only important factor for the reactivity of these trans-alkenes. The reaction rates were also dependent on the steric and electronic properties of the double bond.
520 $a Strained alkenes were also capable of undergoing uncatalyzed migratory insertion reactions with metal-hydride and metal-carbon ?-bonds. 1,2-Hydroalumination and carboalumination reactions proceeded rapidly at room temperature to give new products as single stereoisomers. 1,2-Carboboration reactions of strained alkenes were also possible and yielded air-stable trialkylboranes as single diastereomers. These products could be functionalized to give alcohols with up to five stereocenters in a row.
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773 0 $t Dissertation Abstracts International $g 79-12B(E).
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792 $a 2018
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10745144