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Annulation

Annulation

[an-yuh-lit, -leyt]
Annulation (derived from annular, occasionally annelation) in organic chemistry is a chemical reaction in which a new ring is constructed on another molecule (often another ring).

Examples are the Robinson 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) chloride induced ketone - alkene cyclization of 5-methylenecyclooctanone which proceeds through a ketyl intermediate :

Benzannulation

The term benzannulated compounds refers to derivatives of cyclic compounds (usually aromatic) which are fused to a benzene ring. Examples are listed in the table below:
Benzannulated derivative Source of cyclic compound
Benzopyrene Pyrene
Quinoline Pyridine
Isoquinoline
Chromene Pyran
Isochromene
Indole Pyrrole
Isoindole
Benzofuran Furan
Isobenzofuran
Benzimidazole Imidazole

References

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