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  • Professor Igor Alabugin
    09/26/17 -
    9:45 AM to 11:00 AM

    Department Seminar: Professor Igor V. Alabugin

    Department Seminar

"New ways to solve the Ouroboros puzzle: stereoelectronic control of radical cyclizations and fragmentations"

Alkynes are perfect carbon-rich precursors for the preparation of extended polyaromatics, as long as alkyne reactivity can be controlled and directed.1,2 In this talk, I will present two new synthetic strategies for accomplishing this goal. The first part will illustrate synthetic opportunities arising from the fusion of cyclization cascades with traceless directing groups3 that take advantage of new supramolecular interactions (“radical bonding”). The second part will show how stereoelectronic limitations of alkyne chemistry can be bypassed by coupling cyclizations with fragmentations. This combination allows one to use of alkenes as synthetic equivalents of alkynes.4  

Professor Alabugin's graphic for his seminar Sept. 26

References

  1. Alabugin, I. V.; Gold, B. J. Org. Chem., 2013, 78, 7777.
  2. Alabugin, I. V.;  Gilmore, K.; Manoharan, M. J. Am. Chem. Soc. 2011, 133, 12608.  Alabugin, I. V.;  Gilmore, K. Chem. Commun., 2013, 49, 11246. Gilmore, K; Mohamed, R. K.; Alabugin, I. V. WIREs: Comput. Mol. Sci. 2016, 6, 487.
  3. Pati, K.; dos Passos Gomes, G.; Harris, T.; Hughes, A.; Phan, H.; Banerjee, T.; Hanson, K.; Alabugin, I. V. J. Am. Chem. Soc. 2015, 137, 1165. Harris, T.; Gomes, G.; Clark, R. J.; Alabugin, I. V. J. Org. Chem., 2016, 81, 6007. Pati, K.; Gomes, G.; Alabugin, I. V. Angew. Chem. Int. Ed., 2016, 55, 11633.
  4. Mohamed, R.; Mondal, S.; Gold, B.; Evoniuk, C. J.; Banerjee, T.; Hanson, K.; Alabugin, I. V. J. Am. Chem. Soc., 2015, 137, 6335. Mohamed, R. K.; Mondal, S.; Guerrera, J. V.; Eaton, T.M.;  Albrecht-Schmitt, T. E.; Shatruk, M.;  Alabugin, I. V. Angew. Chem. Int. Ed., 2016, 55, 12054. Evoniuk, C.; Gomes, G. P.; Ly, M.; White, F.; Alabugin, I. V. J. Org. Chem., 2017, 82, 4265.

Research interests

Professor Alabugin’s group is interested in the discovery of new ways to control molecular structure and reactivity. The art of making organic molecules plays an important role in its projects and a solid knowledge of organic synthesis is a critical foundation for every project undertaken by the group. Equally important is the ability to test the feasibility of ideas with quantum-mechanical computations. 

  • Event Details

    Location: 331 Smith Hall
    Host: Professor Thomas Hoye
    Speakers:
    • Professor Igor V. Alabugin
    • Igor Alabugin
    • Department of Chemistry & Biochemistry
    • Florida State University
    • Tallahassee