Amanda C. Jones -- PhD 2007

Scientific Career

Thesis Title
Rapid Injection NMR and Organolithium Reactivity
Research Summary Amanda took the Rapid Injection NMR (RINMR) apparatus developed by Aaron Sanders and modified by Marty Bevan and fine-tuned the system and procedures to make it into a reliable tool for the study of organolithium reagent reactivity. Her focus was mainly on the comparison of reactivity of different aggregates, although she also made significant observation on the comparison between various electrophiles, and on the detailed mechanism of reactions never before examined kinetically.

The largest part of her thesis work was devoted to a study of the reactivity of n-BuLi dimers, tetramers, and several n-BuLi mixed aggregates. She found that in the deprotonation of various acetylenes, the dimer was ca 108 times as reactive as the tetramer, and in the reaction with aldehydes at least 40,000 times as reactive.

Other comparisons, for example of the triple ion and monomer of (Me3Si)3CLi , and the tetramer and monomer of an aryllithium reagents, gave similar enormous reactivity differences of 109 and greater.

After her work at Wisconsin Amanda did two years of postdoctoral work in the Stolz group at CalTech, and then moved to her current faculty position at Wake Forest University.

Papers
  1. "Interconversion of Contact and Separated Ion Pairs in Silyl- and Arylthio-Substituted Alkyllithium Reagents," Hans J. Reich, William H. Sikorski, Jennifer L. Thompson, Aaron W. Sanders, Amanda C. Jones, Org. Lett. 2006, 8, 4003-4006. (Communication) PDF

  2. "Reactivity of Individual Organolithium Aggregates - a RINMR Study of n-Butyllithium and 2-Methoxy-6-(methoxymethyl)phenyllithium," Amanda C. Jones, Aaron W. Sanders, Martin J. Bevan and Hans J. Reich, J. Am. Chem. Soc. 2007, 129, 3492-3493. PDF, Suppl

  3. "Reactivity of the Triple Ion and Separated Ion Pair of Tris(trimethylsilyl)methyllithium with Aldehydes: A RINMR Study," Amanda C. Jones, Aaron W. Sanders, William H. Sikorski, Kristen L. Jansen, Hans J. Reich J. Am. Chem. Soc. 2008, 130, 6060-6061 (communication). PDF, Suppl, DOI

  4. "Multinuclear NMR Study of the Solution Structure and Reactivity of Tris(trimethylsilyl)methyllithium and its Iodine Ate Complex" Hans J. Reich, William H. Sikorski, Aaron W. Sanders, Amanda C. Jones, Kristin N. Plessel J. Org. Chem. 2009, 74, 719-729 (Article) PDF, Suppl, DOI

  5. "A Rapid Injection NMR Study of the Reaction of Organolithium Reagents with Esters, Amides, and Ketones." Kristin N, Plessel, Amanda C. Jones, Daniel J. Wherritt, Rebecca M. Maksymowicz, EricT. Poweleit, and Hans J. Reich Org. Lett., 2015, 17, 2310-2313. (Communication) PDF, Suppl, DOI ACS Editor's Choice

Current Position Assistant Professor at Wake Forest University


Amanda in the lab 2002


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