2 ways to stick nitrogen into alkenes

Reactions that completely break carbon-carbon double bonds have particular transformative power in synthesis. Ozonolysis , which splits one alkene into two carbonyl compounds using trioxygen, is widely used in both industrial and academic settings. And while nitrogen is a valuable component of many natural products, drugs, and agrochemicals, chemists have struggled to come up with an accessible nitrogen-based equivalent to ozonolysis. Now, two teams of chemists working independently have each come up with a new approach to filling the nitrogen-sized hole in the alkene cleavage toolbox. Both methods break carbon-carbon double bonds and install carbon-nitrogen bonds, and both accept a broad collection of starting materials, including natural products, but they work differently and give different products. Bill Morandi’s group at Swiss Federal Institute of Technology (ETH), Zurich, devised an approach that uses an iodine oxidant and ammonium carbamate to turn linear alkenes into nitriles and branched alkenes into amidines (