Wayne S. Goldenberg -- PhD 1999

Scientific Career

Thesis Title
I. The Effects of Intramolecular Chelation on Aryllithium Reagents. II. The Configurational Stability of Silicon- and Sulfur-Substituted Chiral Organolithium Reagents
Research Summary Wayne, following up on work of Biggie Gudmundsson, prepared two series of aryllithium reagents with potential chelating groups in the ortho position capable of forming 5, 6, or 7 amine or ether chelates. Several of the amines were prepared 15N labelled to allow positive identification of Li-N contacts. In addition, Wayne studied several model systems without ortho chelating groups. His work provided clear evidence for the close relationship between chelation and aggregation of these aryllithiums. For example, the spectra below show that for the ortho-dimethylaminoethyl compound the dimer is chelated, but the monomer is not.

Some followup experiments were done by Aaron Sanders.
    Work at the University of Colorado.

  1. "Covalent Binding of Aniline to Humic Substances - Comparison of Nucleophilic Addition, Enzyme Catalyzed, and Metal Catalyzed Reactions by 15N NMR," Thorn, K. A.; Goldenberg, W. S.; Younger, S. J.; Weber, E. J. ACS Symposium Series 1996, 651, 299
  2. "Covalent Binding of Aniline to Humic Substances. 2. 15N NMR Studies of Nucleophilic Addition Reactions," Thorn, K. A.; Pettigrew, P. J.; Goldenberg, W. S. Environ. Sci. Technol. 1996, 30, 2764

    Work at the University of Wisconsin.

  3. "Aggregation and Reactivity of Phenyllithium Solutions," Hans J. Reich, D. Patrick Green, Marco A. Medina, Wayne S. Goldenberg, Birgir Ö. Gudmundsson, Robert R. Dykstra, and Nancy H. Phillips, J. Am. Chem. Soc. 1998, 120, 4035. (Article). PDF Suppl.

  4. "Chelated Aryllithium Reagents -- Ring Size and Chelating Group Effects," Hans J. Reich, Wayne S. Goldenberg, Aaron W. Sanders and C. Christoph Tzschucke Org. Letters 2001, 3, 33-36. (Communication) PDF file

  5. "Amine-Chelated Aryllithium Reagents - Structure and Dynamics." Hans J. Reich, Wayne S. Goldenberg, Birgir Ö. Gudmundsson, Aaron W. Sanders, Klaus J. Kulicke, Katya Simon, and Ilia A. Guzei J. Am. Chem. Soc. 2001, 123, 8087-8079.(Article) PDF Suppl.

  6. "Amine and Ether Chelated Aryllithium Reagents - Structure and Dynamics." Hans J. Reich, Wayne S. Goldenberg, Aaron W. Sanders, Kevin L. Jantzi and C. Christoph Tzschucke, J. Am. Chem. Soc. 2003, 125, 3509 (Full paper). PDF Suppl.

  7. "Pyrrolidine Chelated Aryllithium Reagents," Hans J. Reich, Wayne S. Goldenberg and Aaron W. Sanders, ARKIVOC 2004, (xiii) 97-129 (Full Paper). PDF

    Work at Koehler.

  8. "Too Hot to Handle: An Unusual Exposure of HDI in Specialty Painters," Franklin, P. J.; Goldenberg, W. S.; Ducatman, A. M.; Franklin, E. A. Am. J. Ind. Med. 2000, 37, 431.
Current Position Product manager, Wego Chemical & Mineral Corp
Web address: Wego Chemical and Mineral Corp.

Alexia just got her driver's license Dec 2006. Beginning school Sept. 2008

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