Braslau Research Group

at UC Santa Cruz

Dr. Anna Tsimelzon

Thesis abstract:

  A novel methodology for [n+1] radical annulation using sulfur dioxide as a geminal radical acceptor/donor is described. The exo vs. endo selectivity can be tuned by selecting either a linear or branched allylic sulfide terminating group in the starting material. This methodology provides a novel route to the formation of 5, 6, and 7-membered cyclic sulfones utilizing a radical chain mechanism under very mild conditions.

    A new methodology for the synthesis of the N-alkoxyamines is described. N-Alkoxyamines are useful as initiators in nitroxide mediated “living” free radical polymerization. This procedure utilizes silyl radical abstraction from alkyl halide precursors to prepare N-alkoxyamines inaccessible by other methods. As a demonstration of the utility of this methodology an initiator for nitroxide mediated “living” free radical polymerization was prepared with a fluorescent tag attached to the initiating alkyl radical terminus. This labeled initiator was used to synthesize amphiphilic poly(acrylic acid)-b-polystyrene diblock copolymers, which self-assembled in a THF/buffer solution to form structures that are visible by fluorescence.

Ph.D. 2005: Radical [n + 1] Annulations with Sulfur Dioxide and New Methodolgoy for the Syntrhesis of Specialized N-Alkoxyamines

B.S.  Chemistry, Loyola University of Chicago

Anna has worked at a number of companies in the nanotechnology industry (Intermolecular, Kovio, Invisage, NVS Tecnologies, Svaya Nanotechnologies). She now runs an online chemistry tutoring business:  "Tear Free Chemistry"

Publications with the Braslau Group:

A. Tsimelzon, D. Deamer, R. Braslau,* “Synthesis and Self-Assembly of Amphiphilic Diblock Copolymers using a Fluorescent Labeled N-Alkoxyamine Initiator,” Macromolecular Rapid Communications, 2005, 26, 1872-1877.

A. Tsimelzon, R. Braslau*  "N+1 Radical Annulations with SO2," Journal of Organic Chemistry, 2005, 70, 10854-10859.

R. Braslau,* A. Tsimelzon, and J. Gewandter “A Novel Methodology for the Synthesis of N-Alkoxyamines” Organic Letters, 2004, 6, 2233-2235.


Mark, Anna and Julia, 2007