1,3-dipolar cycloadditions – nitrone/alkene

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

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Making five membered rings with 1,3-dipolar cycloadditions

Cycloadditions involving (4n+2) pi electrons occur thermally, with the Diels-Alder being the prime example. How then could you make a five membered ring using six pi electrons?

The answer comes from using a 1,3-dipole (nitrone) which provides the four-electron component (compare diene). In the example shown, the nitrone oxygen provides 2 electrons from its lone pair and two come from the C=N double bond. Combine the two from the alkene component (dipolarophile) and you have got a five-membered transition state involving six pi electrons.

Richard Windsor – Undergraduate Final Year Project 2008

H. Pellissier, Tetrahedron, 2007, 63, 3235–3285.

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