Nitrone

  A nitrone is the N-oxide of an imine and a functional group in organic chemistry. The general structure is R₁R₂C=NR₃⁺O^- where R₃ is differnt from H.

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A nitrone is 1,3-dipole in 1,3-dipolar cycloadditions. It reacts with alkenes to an isoxazolidine:

One example of this reaction type is the reaction of various Baylis-Hillman adducts with C-Phenyl-N-methylnitrone forming an isoxazolidine in which R₁ is phenyl, R₂ is hydrogen and R₃ is a methyl group ^[1].

Nitrones react with terminal alkynes and a copper salt to beta-lactam. This reaction is also called the The Kinugasa reaction ^[2] for example in this reaction: ^[3]:

The first step in this reaction is a dipolar cycloaddition of the nitrone with the in situ generated copper(I) acetylide to a 5-membered ring structure which rearranges in the second step.

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