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Laxman Gurung and Mark A. Cunningham (Chemistry)
"Synthesis and Mechanistic Studies of Chiral Tin Compounds"
Berea 7th Annual Undergraduate Research and Internship Seminar and The Kentucky Academy of Science, November 10, 2006
This research involves mechanistic studies and the synthesis of chiral tin compounds. Because the C-Sn cleavage reaction by electrophiles is selective in nucleophilic solvents such as methanol, but non-selective in non-nucleophilic solvents, it is feasible to synthesize tetrahedral asymmetrical tin compounds. We have synthesized a series of tetrahedrally substituted chiral tin compounds for the purpose of testing the limits of this reaction for sterically diverse ligands. The SE2 mechanism (shown below) for this reaction provides the potential for expanding its scope to asymmetric synthesis. Results show that this reaction is tolerant of a wide range of sterically demanding ligands (R) and that yields are typically > 90%, with short reaction times.
"Synthesis and Mechanistic Studies of Chiral Tin Compounds"
Berea 7th Annual Undergraduate Research and Internship Seminar and The Kentucky Academy of Science, November 10, 2006
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