Faculty Research Interests:
The study of the structure and reactivity of cyclopropanes has yielded significant insights into the nature of the carbon-carbon bond and has led to unique roles for cyclopropanes in chemistry and biology. Since the publication of two complimentary models for bonding in cyclopropane, the first by F?rster, Coulson and Moffitt in 1939, and another by Walsh in 1947, chemists have recognized that the enhanced p-character of the strained carbon-carbon bonds of cyclopropane should lead to unusually high alkene?like reactivity.
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| (a) F?rster?Coulson?Moffitt model. Carbon-carbon bonds are formed from overlap of ?sp5?-hybridized orbitals emanating from each carbon atom. (b) Walsh model. Carbon-carbon bonds are formed in part from overlap of unhybridized p orbitals emanating from each carbon atom. |
Experimental observations have consistently confirmed this hypothesis. In direct analogy to alkenes, cyclopropanes are susceptible to catalytic hydrogenation to yield acyclic alkanes (Scheme 1(a)), and cyclopropanes can be protonated in strong acid to yield acyclic carbocations (Scheme 1(b)). In recent years, increasingly sophisticated applications of the alkene-like reactivity of cyclopropanes have been disclosed. For instance, mechanism-based inhibitors that rely on the conjugate acceptor-like reactivity of activated cyclopropanes have been designed (Scheme 1(c)).
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Advances in the use of the cyclopropane functional group in chemistry and biology will rely on increasing our understanding of the scope of cyclopropane reactivity. Our lab will test the boundaries of the cyclopropane/alkene analogy by investigating the reactivity of cyclopropanes in new chemical and biological systems. Furthermore, since the reactivity potential of cyclopropanes has not been fully explored, significant opportunities for methodology development remain. My research program will focus on expanding the known reactivity of cyclopropanes, developing cyclopropane-based methodologies to facilitate the synthesis of substructures commonly found in bioactive natural products, and devising new uses for cyclopropanes as probes of biochemical processes. The results of these studies will provide a series of tools for use in synthetic organic chemistry and in chemical biology.
All students who join my laboratory will strengthen their skills in organic synthesis, spectroscopy, and reaction development, and some will have an opportunity to work at the interface of organic chemistry and biochemistry.
Recent Publications:
- Graham, T. J. A.; Burgess, J. M.; Gray, E. E.; Goess, B. C. "An Efficient Synthesis of Grandisol Featuring 1,5-Enyne Metathesis", J. Org. Chem. , 2010, 75, 226-228.
- Goess, B. C. "“The Vilsmeier-Haack Rearrangement” ", In Named Reactions for Ring Formations; Li, J. J., Ed.; John Wiley & Sons: New York, 2010, .
- Goess, B. C. "“The Vilsmeier-Haack Rearrangement” ", In Named Reactions for Ring Formations; Li, J. J., Ed.; John Wiley & Sons: New York, 2010, .
- Goess, B. C. "“The Favorskii Rearrangement” ", In Named Reactions for Ring Formations; Li, J. J., Ed.; John Wiley & Sons: New York, 2010, .
- Goess, B. C. "“The McMurry Coupling” ", In Named Reactions for Homologations, Part 1; Li, J. J., Ed.; John Wiley & Sons: New York, 2009, 268-283.
- Goess, B. C. "“The Pinacol Rearrangement” ", In Named Reactions for Homologations, Part 2; Li, J. J., Ed.; John Wiley & Sons: New York, 2009, 319-333.
