Investigation of Resorcin[4]arenes Upper Rim Functionalization

Macarov, Cristina-Adriana (2018) Investigation of Resorcin[4]arenes Upper Rim Functionalization. Doctoral thesis, University of East Anglia.

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Abstract

The research in this thesis depicts aspects in the area of resorcin[4]arenes upper rim functionalization and presents the importance of this type of structures.

The first chapter covers past and present literature regarding general background and synthetic approaches towards building these cage-like cyclic oligomers, and discusses the possible applications as synthetic enzymes.

Chapter two is separated into two main research areas; (i) preparation of a series of monofunctionalized substrates, attaching on each ring desired groups, such as: amines, esters, ethers, carboxylic acids, alcohols, boronic acids, and (ii) design and synthesis of multifunctionalized resorcin[4]arenes, where we aimed to couple two or more of the mentioned functional groups on each aromatic unit.

In the first part of chapter two, two main strategies for upper rim functionalization are reported; (i) at the phenolic OH, reactions that take place almost quantitative, excepting the Buchwald-Hartwig amination (yield 43-94 %, depending on the primary amine used), and (ii) at the ortho position, where, although the unsatisfying yields, some new compounds were successfully synthesized and characterised.

The second part of chapter two details the attempts to multifunctionalize each aromatic unit, using the same methodologies applied to the preparation of the monofunctionalized precursors. The step was found to be challenging due to steric hindrance and low reactivity of the monosubstituted derivatives, and, despite applying longer time, higher temperature and/or pressure, the targeted structures were unsuccessful.

Chapter three includes the experimental data for all the compounds mentioned in chapter two, with chapter four containing some NMR spectra and crystal structure additional information.

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Bruce Beckett
Date Deposited: 26 Jul 2018 09:26
Last Modified: 26 Jul 2018 09:26
URI: https://ueaeprints.uea.ac.uk/id/eprint/67867
DOI:

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