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Synthesis of new Tröger´s Base derivatives

Karlsson, Josefine (2017) KEMR11 20161
Department of Chemistry
Abstract
This thesis describes the preparation of the previously unknown Tröger´s base mono- and bislactams from Tröger´s base and the transformation via olefination, stereoselective hydrogenation and reduction yielding Tröger´s base derivatives which features functional groups pointing into the interior of its cavity.

The target molecules are two new chiral molecular cleft molecules which may be useful in supramolecular chemistry or as ligands in asymmetric catalysis due to the C2-symmetry, rigidity and sharply folded geometry with a nearly right angle between the planes of the aromatic rings.

This thesis also describes the investigation of finding a higher yielding oxidation method since the reaction from Tröger´s base to Tröger´s... (More)
This thesis describes the preparation of the previously unknown Tröger´s base mono- and bislactams from Tröger´s base and the transformation via olefination, stereoselective hydrogenation and reduction yielding Tröger´s base derivatives which features functional groups pointing into the interior of its cavity.

The target molecules are two new chiral molecular cleft molecules which may be useful in supramolecular chemistry or as ligands in asymmetric catalysis due to the C2-symmetry, rigidity and sharply folded geometry with a nearly right angle between the planes of the aromatic rings.

This thesis also describes the investigation of finding a higher yielding oxidation method since the reaction from Tröger´s base to Tröger´s base-bis-lactam did not proceed with good yield, and in addition the effort to obtain the two target molecules. (Less)
Popular Abstract (Swedish)
Trögers bas upptäcktes först av Julius Tröger 1887, det är en symmetrisk molekyl med fyra stycken sexledade ringar som sitter ihop utan ringspänning. Molekylen är kiral (skiljer sig från sin spegelbild) tack vare de två kväveatomerna som hindras av bryggan mellan dem att röra sig, detta skapar en konkav form och en hydrofob (vattenskyende) ficka i molekylen med de två sexledade ringarna nästan vinkelrätt mot varandra. Dessa olika egenskaper gör molekyler baserade på Trögers bas väldigt attraktiva inom många olika områden inom kemi, och är därför intressant att studera.
Please use this url to cite or link to this publication:
author
Karlsson, Josefine
supervisor
organization
course
KEMR11 20161
year
type
H1 - Master's Degree (One Year)
subject
keywords
organic chemistry, organisk kemi
language
English
id
8898233
date added to LUP
2017-01-09 09:55:12
date last changed
2017-01-09 09:55:12
@misc{8898233,
  abstract     = {This thesis describes the preparation of the previously unknown Tröger´s base mono- and bislactams from Tröger´s base and the transformation via olefination, stereoselective hydrogenation and reduction yielding Tröger´s base derivatives which features functional groups pointing into the interior of its cavity.

The target molecules are two new chiral molecular cleft molecules which may be useful in supramolecular chemistry or as ligands in asymmetric catalysis due to the C2-symmetry, rigidity and sharply folded geometry with a nearly right angle between the planes of the aromatic rings.

This thesis also describes the investigation of finding a higher yielding oxidation method since the reaction from Tröger´s base to Tröger´s base-bis-lactam did not proceed with good yield, and in addition the effort to obtain the two target molecules.},
  author       = {Karlsson, Josefine},
  keyword      = {organic chemistry,organisk kemi},
  language     = {eng},
  note         = {Student Paper},
  title        = {Synthesis of new Tröger´s Base derivatives},
  year         = {2017},
}