Reactive Intermediates

Singlet carbenes incorporating a divalent carbon atom (R–C–R’) have grown from laboratory curiosities and theoreticians’ pet peeves into reagents in the growing field of stable carbene chemistry. Still, the experimental characterization of many simple yet fundamentally important carbenes (e.g., hydroxycarbenes, alkyl carbenes, etc.) is hampered by their high reactivity or lack of precursors. Hydroxycarbenes have been an unknown class of compounds until 2008, when our group reported the synthesis and characteriza­tion of hydroxymethylene (H–C–OH), whose preparation has been chal­lenging organic chemists for more than 80 years. The reaction of hydroxycarbene with formaldehyde would be a source of simple sugars (the so-called “formose reaction” in the origin of life theory). Considerable efforts are ongoing to understand the formation and distribution of simple organics in extraterrestrial environments, and the examination of the structures and reactivities of prototypes such as hydroxycarbene may also provide glimpses of the prebiotic earth.

Director: Univ.-Prof. Peter R. Schreiner

Co-workers:

Dennis Gerbig, David Ley, Hans P. Reisenauer