Johnathan E. Holladay -- PhD 1994

Scientific Career

Thesis Title
Structure and Reactivity Studies of Allenyl-Propargyllithium Reagents
Research Summary John's research set the record straight on the solution structure of allenyl-propargyllithium reagents. He showed using mainly 13C NMR spectroscopy that most of these were localized allenyllithium reagents, but that a few were propargyllithiums.

There were even several that had intermediate structures. Although John found circumstantial evidence that these were mixtures of localized allenyl and propargyllithiums, it was Jennifer Thompson who later provided unambiguous proof of their structure using a Saunder's NMR isotope perturation experiment.

John did postdoctoral work in Scott Denmark's laboratory before moving to his first position at Union Carbide.
Papers
  1. "Synthesis of 2,3-Disubstituted 1,2-Butadienes from Organotin Precursors and Butadienyl Lithium Reagents. Diels-Alder Reactivity", H. J. Reich, I. L. Reich, K. E. Yelm, J. E. Holladay, and D. Gschneidner," J. Am. Chem. Soc. 1993, 115, 6625-35. (Article). PDF

  2. "Lithium-Metalloid Exchange: Reactivity Studies of an Allenyl Lithium Reagent Using an Isomeric Pair of Allenyl and Prop-2-ynyl Stannanes," Hans J. Reich and J. Derek Mason, and Jonathan E. Holladay, J. Chem. Soc., Chem. Commun. 1993, 1481-3. (Communication).

  3. "Solution Structure of Allenyl-Propargyllithium Reagents," Hans J. Reich and Johnathan E. Holladay, J. Am. Chem. Soc. 1995, 117, 8470-71. (Communication) PDF

  4. "The Origin of Regioselectivity in an Allenyllithium Reagent," Hans J. Reich, Johnathan E. Holladay, J. Derek Mason, William H. Sikorski, J. Am. Chem. Soc. 1995, 117, 12137-12150. PDF

  5. "Solution Structure of Silyl-Substituted Allenyl-Propargyllithium Reagents," Hans J. Reich and Johnathan E. Holladay, Angew. Chem. Int. Ed., Engl. 1996, 35, 2365-67. PDF

  6. "Solution Structure and Stereochemistry of Alkyl- and Silyl-Substituted Allenyl-Propargyllithium Reagents," Hans J. Reich, Johnathan E. Holladay, Tamara G. Walker and Jennifer L. Thompson, J. Am. Chem. Soc. 1999, 121, 9769-9780. (Article) PDF

Current Position

For comments, additions and corrections, send e-mail to Hans J. Reich