We have recently demonstrated that, when irradiated with 380 nm light, the singlet ground state of the diamidocarbene (DAC, 1) undergoes excitation to a singlet excited state followed by rapid intersystem crossing to a triplet excited state. If the photolysis is carried out in the presence of aromatic solvents, unprecedented reversible Buchner ring expansion reactions occur. To date, this photochemistry is unique to DACs; indeed, other carbenes including NHCs, cyclic alkyl amino carbenes (CAACs), and mono amido amino carbenes (MAACs), do not exhibit similar reactivity. This presentation will discuss recently discovered photochemical reactions of 1 and another 5 membered DAC, 2. Specifically, we have shown exciting new reactivity including C-H activation of alkanes and silanes, cyclopropanation of arenes, and addition to heteroarenes.

Exploring the photochemistry of diamidocarbenes toward alkanes, silanes, and heteroarenes

Where thousands of chemistry professionals meet to share ideas and advance scientific and technical knowledge. Spring 2023 abstracts, posters, and presentations will launch at the end of March.

ACS Spring 2023

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.