John E. Trend -- PhD 1976

Scientific Career

Thesis Title Physicochemical Studies of Selenoxides and Related Hypervalent Organoselenium Compounds. Nuclear Magnetic Resonance Studies of Organoselenium Compounds, Selenium-77 Chemical Shifts.
Research Summary 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.

Papers
  1. "Synthesis of Thiabicyclo[2.2.2]octenes. Carbon-13 NMR Spectra of Bicyclic Sulfides," H. J. Reich and J. E. Trend, J. Org. Chem. 1973, 38, 2637.

  2. "Organoselenium Chemistry. Addition of Tolueneselenenyl Chloride to Ethylene: Concerning the Reported Isolation of a Stable Episelenurane," H. J. Reich and J. E. Trend, Can. J. Chem. 1975, 53, 1922. PDF

  3. "Stereochemical Dependence of Geminal Selenium-Carbon Coupling Constants," H. J. Reich and J. E. Trend, J. Chem. Soc., Chem. Commun. 1976, 310.

  4. "Organoselenium Chemistry. Mechanism and Stereochemistry of N,N-Dimethylbenzene-selenenamide Addition to Dimethyl Acetylenedicarboxylate. Configurationally Labile Olefins," H. J. Reich, J. M. Renga and J. E. Trend, Tetrahedron Lett. 1976, 2217.

  5. "Organoselenium Chemistry. Intra- and Intermolecular Trapping of Selenenic Acids Formed by Selenoxide Elimination. Formation of A Selenium Ylide," H. J. Reich and J. E. Trend, J. Org. Chem. 1976, 41, 2503.

  6. "Syn Elimination of Alkyl Selenoxides. Side Reactions Involving Selenenic Acids, Structural and Solvent Effects on Rates," H. J. Reich, S. Wollowitz, J. E. Trend, F. Chow and D. F. Wendelborn, J. Org. Chem. 1978, 43, 1697.

Current Position Retired from 3M company ca 09-03
3M Company


For comments, additions and corrections, send e-mail to Hans J. Reich