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Toward a Unified Mechanism for Oxoammonium Salt-Mediated Oxidation Reactions: A Theoretical and Experimental Study Using a Hydride Transfer Model.
Hamlin, Trevor A; Kelly, Christopher B; Ovian, John M; Wiles, Rebecca J; Tilley, Leon J; Leadbeater, Nicholas E.
Affiliation
  • Hamlin TA; †Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269, United States.
  • Kelly CB; †Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269, United States.
  • Ovian JM; †Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269, United States.
  • Wiles RJ; †Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269, United States.
  • Tilley LJ; ‡Department of Chemistry, Stonehill College, 320 Washington Street, Easton, Massachusetts 02357, United States.
  • Leadbeater NE; †Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269, United States.
J Org Chem ; 80(16): 8150-67, 2015 Aug 21.
Article in En | MEDLINE | ID: mdl-26167866
ABSTRACT
A range of oxoammonium salt-based oxidation reactions have been explored computationally using density functional theory (DFT), and the results have been correlated with experimentally derived trends in reactivity. Mechanistically, most reactions involve a formal hydride transfer from an activated C-H bond to the oxygen atom of the oxoammonium cation. Several new potential modes of reactivity have been uncovered and validated experimentally.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Quantum Theory / Quaternary Ammonium Compounds / Models, Chemical Language: En Journal: J Org Chem Year: 2015 Document type: Article Affiliation country: United States
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Quantum Theory / Quaternary Ammonium Compounds / Models, Chemical Language: En Journal: J Org Chem Year: 2015 Document type: Article Affiliation country: United States