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Synthesis of Tröger's Base Analogs from an Aniline Derivative

Klarén, Joel LU (2019) KEML11 20182
Department of Chemistry
Abstract
Functionalization of a TB analogue through a six step synthesis has been performed, collecting valuable material for further synthesis towards a heptakis TB analogue and characterization of intermediates.
Previous work in the Wärnmark group has produced this heptakis TB analogue and this project focused on following the worked out procedure and improving it where possible. The synthesis started from two aniline derivatives that were modified and condensed to a first TB analogue. The following steps were functionalizations of this molecule and finally formation of two diastereomers that were separated using column chromatography, allowing linear condensation in a controlled fashion later on. This work included many different reactions,... (More)
Functionalization of a TB analogue through a six step synthesis has been performed, collecting valuable material for further synthesis towards a heptakis TB analogue and characterization of intermediates.
Previous work in the Wärnmark group has produced this heptakis TB analogue and this project focused on following the worked out procedure and improving it where possible. The synthesis started from two aniline derivatives that were modified and condensed to a first TB analogue. The following steps were functionalizations of this molecule and finally formation of two diastereomers that were separated using column chromatography, allowing linear condensation in a controlled fashion later on. This work included many different reactions, such as condensations, TMS protection, Buchwald-Hartwig amination, and electrophilic aromatic substitution. (Less)
Popular Abstract
The field of supramolecular chemistry is the study of intramolecular forces, or how molecules interact and bind to each other with weak bonds, different from covalent bonds which are usually what comes to mind when the word “chemical bond” is mentioned. Examples of such weak bonds are hydrogen bonds and van der Waals forces.
An interesting molecule in this aspect is Tröger’s base (TB), which is a V-shaped molecule consisting of two aromatic rings fused together with a diazocine ring. The shape of TB gives it an electron-rich cavity which might give the molecule interesting properties in catalysis, speeding up desired reactions for example. The Wärnmark group has performed linear condensation of several TB analogs to create two different... (More)
The field of supramolecular chemistry is the study of intramolecular forces, or how molecules interact and bind to each other with weak bonds, different from covalent bonds which are usually what comes to mind when the word “chemical bond” is mentioned. Examples of such weak bonds are hydrogen bonds and van der Waals forces.
An interesting molecule in this aspect is Tröger’s base (TB), which is a V-shaped molecule consisting of two aromatic rings fused together with a diazocine ring. The shape of TB gives it an electron-rich cavity which might give the molecule interesting properties in catalysis, speeding up desired reactions for example. The Wärnmark group has performed linear condensation of several TB analogs to create two different heptakis TB analogues which can form a zigzag or a tubular structure. These structures may prove useful in catalysis or as molecular receptors.
This work has followed the procedures developed by earlier work in the group, functionalizing a TB analogue, preparing for a final linear fusion to the heptakis TB. Starting from an aniline derivative, condensation yielded a TB analogue which was then modified and functionalized in a series of reactions. (Less)
Please use this url to cite or link to this publication:
author
Klarén, Joel LU
supervisor
organization
course
KEML11 20182
year
type
M2 - Bachelor Degree
subject
keywords
Tröger's Base, Supramolecular chemistry, Organic synthesis, Organic chemistry, Organisk kemi
language
English
id
8991126
date added to LUP
2019-08-19 13:31:26
date last changed
2019-08-19 13:31:26
@misc{8991126,
  abstract     = {{Functionalization of a TB analogue through a six step synthesis has been performed, collecting valuable material for further synthesis towards a heptakis TB analogue and characterization of intermediates.
Previous work in the Wärnmark group has produced this heptakis TB analogue and this project focused on following the worked out procedure and improving it where possible. The synthesis started from two aniline derivatives that were modified and condensed to a first TB analogue. The following steps were functionalizations of this molecule and finally formation of two diastereomers that were separated using column chromatography, allowing linear condensation in a controlled fashion later on. This work included many different reactions, such as condensations, TMS protection, Buchwald-Hartwig amination, and electrophilic aromatic substitution.}},
  author       = {{Klarén, Joel}},
  language     = {{eng}},
  note         = {{Student Paper}},
  title        = {{Synthesis of Tröger's Base Analogs from an Aniline Derivative}},
  year         = {{2019}},
}