Brief Overview of Research

General Research Areas:

1) Polyyne Synthesis and Bioactivity. Rather than examine derivatives of naturally-occurring diynes, we synthesized simpler analogues to determine the structural features that might be necessary for biological activity. We are currently pursuing additional funding to continue this work. See "Polyynes and Biological Activity" for more details.

2) Alkyne-Prins Reactions. Though the normal Prins reaction involving alkene additions to oxocarbenium ions has been known for over 100 years, the alkyne-Prins variant has been far less utilized. In particular, we are creating novel molecules using oxocarbenium ion and iodonium ion intermediates in cascade, or domino reaction sequences involving alkyne-Prins cyclizations. These complex processes involve a number of discreet organic transformations in which the individual reactions must take place in a specific order for the overall reaction to afford products in reasonable yields. In essence, one reaction (domino) must proceed before the next react reaction can take place (fall), and so-on. For more details, see "Alkyne-Prins Cascade Chemistry" for further details.

Typical Lab Work:

Much of the work in the Hinkle Lab revolves around synthesizing, purifying, and analyzing a wide variety of organic molecules. In order to do these things, we do a variety of reactions under low-temperature, moderate pressure, and high temperature conditions. Most reactions require a typical "workup" (i.e., addition of an aqueous "quench" of intermediates followed by an extraction) to get crude materials. We then typically use column chromatography as a purification technique. We also are among the most frequent users of the 400 MHz NMR spectrometer and generally obtain 1H, 13C, 13C(APT), COSY, and HSQC NMR spectra for all new compounds. The late Professor Hans Reich at the University of Wisconsin, Madison maintained a fabulous site for NMR Spectroscopy. Further, Prof. James Nowick at UC, Irivine, has an excellent worksheet on splitting patterns.

Though all techniques we use are widely used in most synthetic chemistry labs, the techniques do take quite a bit of time and practice to do well. As with most labs, nearly all students begin in my lab by shadowing a senior group member ... typically someone who's already worked for an entire summer in the lab.

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