Genuine carbene versus carbene-like reactivity

Abstract

Singlet carbenes are not always isolable and often even elude direct detection. When they escape observation, their formation can sometimes be evidenced by in situ trapping experiments. However, is carbene-like reactivity genuine evidence of carbene formation? Herein, using the first example of a spectroscopically characterized cyclic (amino)(aryl)carbene (CAArC), we cast doubt on the most common carbene trapping reactions as sufficient proof of carbene formation.

Keywords: CAArC; CMD; DFT; carbenes; chalcogens.