Associate Professor of Chemistry Max Majireck and members of his research group recently published an article in The Journal of Organic Chemistry, an American Chemical Society publication. “Synthesis of Bench-Stable N-Quaternized Ketene N,O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis” is the result of four years of work involving 20 Hamilton student co-authors from the classes of 2017 through 2023.
The article describes in detail the production of a rare class of compounds originally discovered in Majireck’s lab. Majireck said these compounds belong to a broader category called N-quaternized ketene N,O-acetals and are generally regarded as being too unstable to isolate. For that reason he said, their use as a reagent (a substance used in chemical reactions) has been largely overlooked.
The team discovered a new way to make stable versions of these compounds and provided more than 40 examples in their article, significantly expanding the availability of this understudied but highly valuable material for future research. In addition, the team identified multiple new reaction types involving the compounds, which they believe will be adopted by other synthetic chemists for a range of new applications such as drug or material synthesis.
“I’m particularly proud that such a large team of undergraduates contributed to this project over the years,” Majireck said. “It’s a testament to their hard work and skill in the lab that every new student who joined the project could easily replicate the results of prior students. They developed a robust set of procedures that both a novice and experienced chemist can execute.
“I’m really excited to build off of this foundational study to find even more applications of N-quaternized ketene N,O-acetals with a new generation of Hamilton students,” Majireck added.
Members of Majireck's research group who contributed to the article are Danielle L. McConnell ’20, Alisha M. Blades ’20, Danielle Gomes Rodrigues ’19, Phoebe V. Keyes ’19, Justin C. Sonberg ’18, Caitlin E. Anthony ’18, Sofia Rachad ’18, Olivia M. Simone ’19, Caroline F. Sullivan ’20, Jonathan D. Shapiro ’17, Christopher C. Williams ’17, Benjamin C. Schafer ’17, Amy M. Glanzer ’21, Holly L. Hutchinson ’21, Ashley B. Thayaparan ’21, Zoe A. Krevlin ’22, Isabella C. Bote ’22, Yasin A. Haffary ’23, Sambat Bhandari ’23, and Jack A. Goodman ’18.
This research was sponsored by Hamilton’s Edward and Virginia Taylor Fund and the Dean of Faculty’s Office, and individual support provided by the Kirkland Endowment allowed several student co-authors to present the research at conferences. Support for an additional summer research student who helped to complete the project was provided by Organic Syntheses, Inc.