Nitroalkene

A nitroalkene, or nitro olefin, is a functional group combining the functionality of its constituent parts, an alkene and nitro group, while displaying its own chemical properties through alkene activation, making the functional group useful in specialty reactions such as the Michael reaction or Diels-Alder additions.

[1] Nitroalkenes are synthesized by various means, notable examples include: Nitroalkenes are useful intermediates for various chemical functionalities.

The related nitroalkynes are rather unstable, easily losing nitrogen dioxide radicals, rearranging to nitriles over −40 °C, or adding nucleophiles.

In contrast, Tilden's reagent suffices to nitrosylate metalloalkynes; the products then oxidize to nitroalkenes in peroxyacids.

Protected nitroalkene dehydroiodination occurs delicately in the gas phase.