Laboratory Insider: A Look Inside the Organic Synthesis Lab
Ask the Expert Webinar
Presented live November 2, 2022
Step inside the Parasram Lab at New York University for a look at some of their latest research.
In this webinar, Professor Marvin Parasram will discuss data from his laboratory’s recent publication, “Anaerobic Heteroatom Transfer Reactions Using Photoexcited Nitroarenes.” The research features developments on the anaerobic cleavage of alkenes into carbonyl compounds using nitroarenes as oxygen transfer reagents under visible light. This approach is a safe and practical alternative to mainstream oxidative cleavage protocols, such as ozonolysis and the Lemieux–Johnson reaction.
As an attendee, you will learn more about:
- How a wide range of alkenes possessing oxidatively sensitive functionalities underwent anaerobic cleavage to generate carbonyl derivatives with high efficiency and regioselectivity, using the Advion Interchim Scientific puriFlash® 5.250 Preparative HPLC system.
- Mechanistic studies support that the transformation occurs via direct photoexcitation of the nitroarene followed by a nonstereospecific radical cycloaddition event with alkenes.
How this process leads to 1,3,2- and 1,4,2-dioxazolidine intermediates that fragment to give the carbonyl products, using the Advion Interchim Scientific expression Compact Mass Spectrometer.
- How a combination of radical clock experiments and in situ photoNMR spectroscopy revealed the identities of the key radical species and the putative aryl dioxazolidine intermediates, respectively.Watched the video and ready to learn more?