There was some favoritism in choosing my favorite organic molecule, as I have been working with this reagent over the summer in one of the research labs. I specifically picked this molecule because I remember the first day I was shown the full out structure of Phenyl Hypervalent Iodonium Alkynyl Triflate. Coming straight from Gen Chem into an Organic Synthesis research lab was like a smack in the face.
Dr. Peter J. Stang was the first to demonstrate the use of HIATs from the synthesis to the reactivity of these electrophilic species. Unlike other molecules, Ph-HIAT doesn't boast any "daily use" or medical aspects. But, synthesizing this molecule is difficult (and I find it really cool). I've been able to watch it happen, and the equipment compilation alone requires some practice. Ph-HIAT, specifically has to be filtered while no oxygen is present. Another complexity of this synthesis is the temperature requirements, in order for the reaction to even work the temperature has to be atleast -40°C. Then after all of that the HIAT still has to be isolated. Which is finally where I come in to use it after all the tough stuff has been done to use for my reactions. My specific project focuses on a pathway to react Tetrabutyl Ammonium Azide with several different alkenes to create cyanocarbenes, and Ph-HIAT (most recently n-Pentyl HIAT) is one of the reactants in these cyclopropanations.
I F Dempsey Hyatt, Daniel J Nasrallah, Mitchell P Croatt
Department of Chemistry and Biochemistry, University of North Carolina at Greensboro.
Journal of Visualized Experiments 01/2013; DOI: 10.3791/50886
Source: PubMed
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