Reagent-Dictated Site Selective Hydrocarbon Functionalization Using Nitrogen-Centered Radicals Public Deposited

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  • March 20, 2019
Creator
  • Carestia, Anthony
    • Affiliation: College of Arts and Sciences, Department of Chemistry
Abstract
  • Chapter 1. Aliphatic C-H Functionalization An overview of aliphatic radical C-H functionalization is presented with an emphasis on the challenge of site selectivity. Methods covered range from simple, unselective free radical halogenation to highly regioselective biomimetic oxidation. Primary selective functionalizations using electrophilic metal catalysts are also discussed. Chapter 2. Reagent-Dictated Site-Selective C-H Chlorination The development of a site-selective C-H chlorination is discussed. Primary site selectivity is achieved using highly hindered N-chloroamide reagent used. A computational study of the generated amidyl radical structure and the transition state of the selectivity-determining hydrogen-atom abstraction were completed. Chapter 3. Primary Selective C-H Functionalization of Polyolefins A complementary method of polyolefin xanthylation was developed. The regioselectivity of the reaction favors 1° functionalization over 2° functionalization, in stark contrast to the method previously developed by our group. Altering regioselectivity was shown to affect thermal properties in functionalized polyolefins.
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  • In Copyright
Advisor
  • Frankowski, Kevin
  • Alexanian, Erik
  • Leibfarth, Frank
  • Meek, Simon
  • Johnson, Jeffrey
Degree
  • Doctor of Philosophy
Degree granting institution
  • University of North Carolina at Chapel Hill Graduate School
Graduation year
  • 2018
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