Skip to main content
Skip to main menu Skip to spotlight region Skip to secondary region Skip to UGA region Skip to Tertiary region Skip to Quaternary region Skip to unit footer


Macrocyclic 1,4-Diketones: Versatile Intermediates for the Chemical Synthesis of Complex, Congested and Constrained Molecules

Bradley L. Merner
Auburn University
Chemistry Building, Room 400
Organic Seminar

Our group has recently demonstrated that macrocyclic 1,4-dketones can be converted into highly

strained arene-bridged systems, which represent (macrocyclic) benzenoid segments of armchair

carbon nanotubes (CNTs). This non-cross-coupling-based approach enables the incorporation of

strategically placed (aryl) halides that can later be engaged in programmed carbon-carbon bond

forming reactions, resulting in longitudinal pi-extension of benzenoid CNT segments to polycyclic

aromatic hydrocarbon (PAH) segments. The success of this approach is due to a

diastereoselective Grignard reaction, which is, in turn, dependent on the size of the macrocyclic

system(s) employed. Recent work that takes advantage of this size-dependent

diastereoselectivity and its application to the synthesis of functionalized bent arene units, highly

strained benzenoid macrocycles, and polyfunctionalized cyclobutanes will be discussed.

Support Us

We appreciate your financial support. Your gift is important to us and helps support critical opportunities for students and faculty alike, including lectures, travel support, and any number of educational events that augment the classroom experience. Click here to learn more about giving.

Every dollar given has a direct impact upon our students and faculty.

Got More Questions?

Undergraduate inquiries: 

Registration and credit

AP Credit, Section Changes, Overrides,

Graduate inquiries:

Contact Us!

Assistant to the Department Head: Donna Spotts, 706-542-1919 

Main office phone: 706-542-1919 

Main Email:

Head of Chemistry: Prof. Jason Locklin