Studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis

The work described herein encompasses a few topics related to the studies of isomeric phospholes. Phospholes have been explored thoroughly over the past many years. They are now accepted as only weakly aromatic: the aromatic stabilization resulting from electronic delocalization of phosphole’s plana...

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Main Author: Ciric, Ana
Other Authors: School of Physical and Mathematical Sciences
Format: Theses and Dissertations
Language:English
Published: 2012
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Online Access:https://hdl.handle.net/10356/50490
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-504902023-02-28T23:42:48Z Studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis Ciric, Ana School of Physical and Mathematical Sciences Francois Mathey DRNTU::Science::Chemistry The work described herein encompasses a few topics related to the studies of isomeric phospholes. Phospholes have been explored thoroughly over the past many years. They are now accepted as only weakly aromatic: the aromatic stabilization resulting from electronic delocalization of phosphole’s planar state is not sufficient enough to overcome its intrinsically high inversion barrier of phosphorus. This results in their pyramidal structure when in ground state and a very poor orbital overlap between the phosphorus lone pair np and the π orbitals of the diene unit. Therefore, they seem to resemble more cyclopentadienes than their nitrogen analogues - pyrroles. Though, only recently has the attention been shifted to the phosphole’s isomeric form - phospholene. Due to phosphole’s low aromaticity, there lies the opportunity to switch from slightly aromatic to slightly antiaromatic character of these heterocycles, which in turn changes the chemistry of this species. DOCTOR OF PHILOSOPHY (SPMS) 2012-06-06T02:52:37Z 2012-06-06T02:52:37Z 2012 2012 Thesis Ciric, A. (2012). Studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/50490 10.32657/10356/50490 en 105 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry
spellingShingle DRNTU::Science::Chemistry
Ciric, Ana
Studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis
description The work described herein encompasses a few topics related to the studies of isomeric phospholes. Phospholes have been explored thoroughly over the past many years. They are now accepted as only weakly aromatic: the aromatic stabilization resulting from electronic delocalization of phosphole’s planar state is not sufficient enough to overcome its intrinsically high inversion barrier of phosphorus. This results in their pyramidal structure when in ground state and a very poor orbital overlap between the phosphorus lone pair np and the π orbitals of the diene unit. Therefore, they seem to resemble more cyclopentadienes than their nitrogen analogues - pyrroles. Though, only recently has the attention been shifted to the phosphole’s isomeric form - phospholene. Due to phosphole’s low aromaticity, there lies the opportunity to switch from slightly aromatic to slightly antiaromatic character of these heterocycles, which in turn changes the chemistry of this species.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Ciric, Ana
format Theses and Dissertations
author Ciric, Ana
author_sort Ciric, Ana
title Studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis
title_short Studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis
title_full Studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis
title_fullStr Studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis
title_full_unstemmed Studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis
title_sort studies of isomeric phospholes : synthesis and application in transitionmetal and organic catalysis
publishDate 2012
url https://hdl.handle.net/10356/50490
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