Title page for ETD etd-02262016-201516

Type of Document Dissertation
Author Ayala, Caitlan Elizabeth
Author's Email Address cayala1@lsu.edu
URN etd-02262016-201516
Title Contemporary Organic Transformations Enabled by Novel Cationic Processes
Degree Doctor of Philosophy (Ph.D.)
Department Chemistry
Advisory Committee
Advisor Name Title
Allen, Austin Committee Member
Ragains, Justin Committee Member
Stanley, George Committee Member
Vicente, Graca Committee Member
  • synthetic methods
  • oxyallyl cation
  • chlorination
Date of Defense 2016-02-18
Availability unrestricted
This dissertation focuses on the development of synthetic methodologies in organic synthesis in two different areas. Chapter 1 discusses the more recent examples of transforming alcohols to their corresponding alkyl chlorides. The first area of our group’s research interest is the development of a mild chlorination method from unactivated alcohols, detailed in Chapter 2.

Chapter 3 provides an insight into the history of oxyallyl cations, the basis of the second methodology development project in our laboratory. This chapter focuses on the traditional reactions that utilize these reactive intermediates, and it also showcases the concept of direct nucleophilic addition and the applications of the á-indole ketones. Chapters 4 through 7 detail the discovery and development of a novel method involving the use of “protected” oxyallyl cation intermediates. In these chapters, the reactivity of starting materials, nucleophilic additives, solvents, and catalysts are described in regards to the formation of a variety of distinctive small molecules.

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