|Thesis Title||Physicochemical Studies of Selenoxides and Related Hypervalent Organoselenium Compounds. Nuclear Magnetic Resonance Studies of Organoselenium Compounds, Selenium-77 Chemical Shifts.|
John joined the group during my first year at Wisconsin. He quickly became the NMR expert, and performed a series of studies which made effective use of his expertise, including the discovery of two major errors in published reports of organosulfur and selenium structures. |
A central theme of John's work was the stereochemistry of selenoxides, where he showed that selenoxide inversions are many orders of magnitude faster than sulfoxide analogs, and proceed by three pathways - through the neutral selenoxide, as well as through the monoprotonated and diprotonated forms.
John also discovered that the decomposition products of selenoxides, transient selenenic acids, were good electrophiles, and easily added to olefins, either inter- or intramolecularly. This discovery was of considerable importance in debugging synthetic applications of selenoxide eliminations and [2,3]sigmatropic rearrangements, concurrently and subsequently studied by Sue Wollowitz, Shrenik Shah, Flora Chow , Rick Olson, Bill Willis, Debra Saez and others.
Retired from 3M company ca 09-03|