Mechanistic Determination of Tautomerization of Carbamoyl Derivatives of Tröger’s Base

Trey A. Maddaleno
Dr. Stuart Winikoff, Faculty Mentor

Tröger’s base (2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine) is of interest due to its capacity as a flexible organic building block, with additional utility as a dopant in LCD screens. Previous experimental work has developed processes to modify Tröger’s base with a number of substituents, particularly carbamoyl groups, with the resulting derivatives existing as two enantiomers. We’re interested in the process of tautomerization between these two enantiomers using a diisopropylamine and n-butyllithium mixture with subsequent protic quenching. By using computational methods, we hope to verify the mechanism by which this reaction occurs and use this information to better control stereochemistry.

Keywords: Computational Chemistry, Tröger’s base, Mechanism

Topic(s):Chemistry

Presentation Type: Oral Presentation

Session: TBA
Location: TBA
Time: TBA