Research Interests

Organic chemistry of hypervalent iodine
My research is primarily in the area of organic compounds based on hypervalent iodine. This interesting group of molecules includes [hydroxy-(tosyloxy)iodo]benzene (Koser's reagent, HTIB), iodobenzene diacetate, and the Dess-Martin periodane. These and many related compounds have achieved the status of "reagent" in contemporary synthetic methods. Due to the higher oxidation state of iodine, these compounds act as mild oxidants capable of an ever expanding scope of synthetic applications. With the recent interest in "green" methods of organic synthesis my focus is the development and study of a cyclic analog of HTIB, 1H-1-hydroxy-1,2,3-benziodoxathiole 3,3-dioxide or HMBI. When an oxidant such as HTIB is used, it becomes reduced, in this case to iodobenene and p-toluenesulfonic acid. In a synthetic procedure this requires an aqueous workup to remove the acid, and often column chromatography to remove the iodobenzene. Due to the high vapor pressure of iodobenzene it is partially lost in concentration under vacuum and is rarely collected and reused or even disposed of properly!

HMBI only yields upon reduction a iodinated toluenesulfonic acid, which can be recovered quantitatively and reused. In fact, the HMBI used for my current research is reoxidized and reutilized reagent from earlier projects!

An example from the research of Michelle Borkovec (Class of '07):

This reagent is very applicable to the undergraduate reseach program here at Behrend. With the simplified work-up procedures this reagent offers, an undergraduate can spend more of their limited time doing research focused on reaction outcome and product separation and distribution rather than tedious and repetitive workup procedures for the reagent itself.

 

 

 

Hypervalent Iodine

While the idea of "hypervalent" iodine compounds may seem a difficult concept at first, the chemistry is easily related to the core concepts of basic organic chemistry.

For example, [hydroxy-(tosyloxy)iodo]benzene (HTIB) or Koser's reagent bascically functions as a highly evolved bromine analog. If you can think of a reaction of elemental bromine with an organic compound, you already know one of the reactions of HTIB!