CAREER: Generation of Cyanocarbenes from Alkynes and Azides

University Of North Carolina Greensboro, Greensboro NC

Investigators

Abstract

For this project, Professor Mitchell P. Croatt in the Department of Chemistry and Biochemistry at the University of North Carolina at Greensboro is funded by the Chemical Structure, Dynamics and Mechanisms B Program of the Chemistry Division to investigate the synthesis and reactions of cyanocarbenes made from alkynes and azides. The goal of the project is to use readily available compounds, have them undergo previously unexplored reaction mechanisms, and generate products with significantly increased molecular complexity. An educational goal of this project is to develop a program to help students learn organic chemistry better and more quickly train them to visualize molecules as if they were experienced organic chemists. The program is designed to create a game-like atmosphere to make learning organic chemistry fun while also helping students to learn the material more efficiently. Finally, training of underrepresented minority researchers will actively take place through a variety of methods including a series of discussion panels. This project explores the conversion of electrophilic alkynes and nucleophilic azides to cyanocarbenes and then studies their subsequent reactivity. The electrophilic alkynes, hypervalent iodonium alkynyl triflates, are isolable. However, this project will form them in situ and allow them to react with azide anions. A series of reactive intermediates, including vinylidene carbenes and alkynyl azides, are formed, and eventually cyanocarbenes are generated. These electrophilic carbenes will be allowed to react with a variety of nucleophiles to produce additional reactive intermediates which can undergo extensive rearrangement before producing stable molecules with significantly increased molecular complexity.