34th Annual Student Research Conference
Mechanistic Determination of Isomerization for Carbamoyl Derivatives of Tröger’s Base
Trey A. Maddaleno
Dr. Stuart Winikoff, Faculty Mentor
Derivatives of Tröger’s base (2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine) are valuable targets of study in catalysis, but their synthesis often produces the less desirable exo enantiomer in excess. Previous experimental study in Mizzou’s Harmata group has developed processes to modify Troger’s base with a number of substituents, particularly carbamoyl groups. Of particular interest is their development of an isomerization reaction between the endo and exo enantiomers using a diisopropylamine and n-butyllithium mixture with subsequent protic quenching. By modelling this reaction with density functional theory, the mechanism by which the reaction occurs can be verified, with this information lending to a better understanding of the molecules’ stereochemistry. Results indicate that steric forces associated with nitrogen substituents play a defining role in the reaction.
Keywords: DFT, computational chemistry, modelling
Topic(s):Chemistry
Presentation Type: Asynchronous Virtual Oral Presentation
Session: 6-10
Location: https://flipgrid.com/ebc10430
Time: 0:00