Molecular oxygen is an ideal source of oxygen atoms for synthetic transformations because it is inexpensive, abundant, and non-toxic. This dissertation presents the development of synthetic methods to oxidize alkenes to α-oxygenated ketones, hydroperoxides, alcohols, and endoperoxides using molecular oxygen under transition-metal or ambient-light catalysis. Chapter One describes a copper-catalyzed method to afford α-oxygenated ketones that can be further functionalized to give a variety of products. Chapter Two offers a light-catalyzed method for the synthesis of hydroperoxides from enol ethers and strained alkenes. Chapter Three discusses a cobalt-catalyzed synthesis of 1,2-dioxolanes and their applications in cancer biology. Chapter Four presents preliminary work in the construction of 1,2-dioxanes, which can be manipulated to furnish biologically active natural product derivatives.
|Advisor:||Woerpel, Keith A.|
|Commitee:||Buccella, Daniela, Diao, Tianning, Mahal, Lara, Turner, Daniel|
|School:||New York University|
|School Location:||United States -- New York|
|Source:||DAI-B 80/03(E), Dissertation Abstracts International|
|Subjects:||Chemistry, Organic chemistry|
|Keywords:||1,2-dioxanes, 1,2-dioxolanes, Hydroxylamines, Molecular oxygen, Peroxides|
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