|Thesis Title||Chemistry of Selenones.|
Debbie investigated the preparation, properties and reactions of selenones, the selenium analogs of sulfones. This chemistry had, up to that time, been essentially undeveloped. She found that many of the selenones that had been reported were actually other compounds, and developed procedures for the preparation of authentic ones. Selenones turned out to be much more polar than sulfones, were more acidic by several pKa units, and were excellent alkylating agents. For example, methyl phenyl selenone was an order of magnitude more reactive than methyl iodide as an alkylating agents towards dimethyl sulfide (to form trimethylsulfonium).
She also discovered that selenones underwent a "selenone syn elimination," analogous to the selenoxide elimination, a reaction that is unknown for sulfones.
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