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New Carbenoid Species Yields Unexpected Reactivity

The 'radical carbenoid' allows stereoconvergent cyclopropanation reaction

© ICIQ / © Wiley-VCHToday, chemists synthesize cyclopropanes using pure E or Z alkenes as starting materials and usually, dangerous, unstable reagents such as diazomethane or iodomethylzinc iodide.

Now, a team of researchers led by Dr. Suero at the Institute of Chemical Research of Catalonia in Tarragona (Spain) has designed a new strategy that allows the stereoconvergent preparation of trans-cyclopropanes starting from E/Z alkene mixtures. Moreover, this photoredox catalytic method uses diiodomethane -a commercially available, easy to handle reagent- as the methylene source.

This research represents the first example of a stereoconvergent cyclopropanation reaction. It is also the first proposal of a new type of carbenoid species, dubbed 'radical carbenoid', theoretically equivalent to a triplet carbene but with a completely unprecedented reactivity.