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Multistep reactions based on thiolactones for the synthesis of functionalized polymers

(2015)
Author
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(UGent)
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Abstract
The aim of this research project was to develop a method for the synthesis of advanced polymeric structures without the use of timeconsuming protecting group strategies. The proposed method is based on the reaction between thiols and unsaturated carbon chains, denoted as thiol-ene or thiol-yne chemistry. Because of the disadvantages of working with thiols (i.e. unpleasant smell, limited commercial availability and instability due to oxidation reactions), there has been a continuous interest in the development of new ways to protect thiols, e.g. as disulfide, thiocarbonylthio-group or methanesulfonate. However, most of these methods require a protecting and a deprotecting step, which is unfavorable in terms of atom-efficiency and overall yield. The strategy herein presented, is based on the use of a thiolactone as a precursor for a thiol, allowing for the direct introduction of a thiol, starting from stable amino compounds without the need for a subsequent deprotection step. Using thiolactones in polymer synthesis has a dual advantage: On the one hand, it offers a chemoselective, atom-efficient way of generating thiols, while at the same time it is possible to introduce functionality via the amine compound. This one-pot amine-thiol-ene conjugation reaction was used for the synthesis and modification of diverse polymeric systems.
Keywords
synthesis, Polymer chemistry, chemistry

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Citation

Please use this url to cite or link to this publication:

Chicago
Goethals, Fabienne. 2015. “Multistep Reactions Based on Thiolactones for the Synthesis of Functionalized Polymers”. Ghent, Belgium: Ghent University. Faculty of Sciences.
APA
Goethals, Fabienne. (2015). Multistep reactions based on thiolactones for the synthesis of functionalized polymers. Ghent University. Faculty of Sciences, Ghent, Belgium.
Vancouver
1.
Goethals F. Multistep reactions based on thiolactones for the synthesis of functionalized polymers. [Ghent, Belgium]: Ghent University. Faculty of Sciences; 2015.
MLA
Goethals, Fabienne. “Multistep Reactions Based on Thiolactones for the Synthesis of Functionalized Polymers.” 2015 : n. pag. Print.
@phdthesis{6920116,
  abstract     = {The aim of this research project was to develop a method for the synthesis of advanced polymeric structures without the use of timeconsuming protecting group strategies. The proposed method is based on the reaction between thiols and unsaturated carbon chains, denoted as thiol-ene or thiol-yne chemistry. Because of the disadvantages of working with thiols (i.e. unpleasant smell, limited commercial availability and instability due to oxidation reactions), there has been a continuous interest in the development of new ways to protect thiols, e.g. as disulfide, thiocarbonylthio-group or methanesulfonate. However, most of these methods require a protecting and a deprotecting step, which is unfavorable in terms of atom-efficiency and overall yield. The strategy herein presented, is based on the use of a thiolactone as a precursor for a thiol, allowing for the direct introduction of a thiol, starting from stable amino compounds without the need for a subsequent deprotection step. Using thiolactones in polymer synthesis has a dual advantage: On the one hand, it offers a chemoselective, atom-efficient way of generating thiols, while at the same time it is possible to introduce functionality via the amine compound. This one-pot amine-thiol-ene conjugation reaction was used for the synthesis and modification of diverse polymeric systems.},
  author       = {Goethals, Fabienne},
  language     = {eng},
  pages        = {IX, 212},
  publisher    = {Ghent University. Faculty of Sciences},
  school       = {Ghent University},
  title        = {Multistep reactions based on thiolactones for the synthesis of functionalized polymers},
  year         = {2015},
}