| |
| author |
Caroline Tramontana
| | title |
Protocol Development for the Synthesis and Application of Samarium Diiodide Using Schlenk Line Techniques
| | abstract |
Samarium diiodide (SmI2) is a useful reagent used in synthetic chemistry laboratories.
SmI2 is a chemoselective single electron reductant that mediates radical reactions, redox
reactions, and carbon-carbon bond-forming reactions.1-5 Despite its versatility, SmI2 is rarely
used in undergraduate laboratories due to its sensitivity to air and water, both of which inactivate
the compound. To combat these sensitivities, it is general practice that all reagents are distilled
and degassed, glassware is dried in the oven, and SmI2 is synthesized and utilized in a glove box
under inert conditions; however, glove boxes are expensive and may be difficult to obtain,
especially for an undergraduate laboratory. A Schlenk line is a lower-cost alternative that creates
micro inert environments within the glassware by vacuuming out all of the air in the glassware
and purging it with an inert gas such as argon or nitrogen. The goal of this laboratory was to
develop a protocol for the synthesis and application of SmI2 using a Schlenk line so it may be
used with ease in laboratories without gloveboxes. Various steps and procedures for the synthesis
of SmI2 were investigated to develop a simple, robust protocol that yielded consistent results.
Using the protocol we developed, SmI2 was consistently synthesized as a 0.1 M solution using
Kagan's method and afforded high conversions of ketones (98% conversion). This protocol will
enable undergraduate laboratories to synthesize and employ SmI2 in more reactions due to its
ease of use on the Schlenk line and consistent results.
| | school |
The College of Liberal Arts, Drew University
| | degree |
B.S. (2022)
|
| advisor |
Dr. Kimberly Choquette
|
| committee |
Dr. Vincent Gullo
Dr. James Supplee
|
| full text | CTramontana.pdf |
| |
