Thesis
Oxidations with endocyclic peroxides and their derivatives
- Creator
- Rights statement
- Awarding institution
- University of Strathclyde
- Date of award
- 2016
- Thesis identifier
- T14421
- Person Identifier (Local)
- 201256694
- Qualification Level
- Qualification Name
- Department, School or Faculty
- Abstract
- This thesis describes two novel transformations (a method to synthesize alkylidene phthalides and a different approach toward the Baeyer-Villiger oxidation) and the development and mechanistic study of a metal-free oxidation of arenes.Chapter 1 introduces the concept of alkene oxyamination. Synthesis of a series of hydroxylamine derivatives of endocyclic peroxides was undertaken, which were then reacted with nitrogen, sulfur and carbon nucleophiles. This led to the discovery of a new reaction that provides access to alkylidene phthalides, a class of compounds which exhibit interesting biological activity.Chapter 2 describes the development of an alternative approach to the Baeyer-Villiger oxidation, through the reaction of hydrogen peroxide and a nitrile in the presence of a base.Chapter 3 describes direct methods for the formation of new aromatic C-O bonds, followed by the presentation of an organic peroxide mediated approach. Herein, an examination of the mechanism of the reaction of a malonoyl peroxide with an arene is studied through Hammett analysis, isotope labeling experiments, EPR studies, DFT calculations and reactivity patterns.Chapters 4 and 5 present the experimental procedures and analytical data relevant to the three reactions developed.Chapter 6 contains a bibliography.
- Resource Type
- DOI
- Date Created
- 2016
- Former identifier
- 9912536592002996
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