Annulation

In organic chemistry, annulation (from Latin anellus 'little ring'; occasionally annelation) is a chemical reaction in which a new ring is constructed on a molecule.

Not to be confused with Annulment.

Examples are the Robinson annulation, Danheiser annulation and certain cycloadditions. Annular molecules are constructed from side-on condensed cyclic segments, for example helicenes and acenes. In transannulation a bicyclic molecule is created by intramolecular carbon-carbon bond formation in a large monocyclic ring. An example is the samarium(II) iodide induced ketone - alkene cyclization of 5-methylenecyclooctanone which proceeds through a ketyl intermediate:

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