Annulation

Not to be confused with Annulment.

In organic chemistry annulation (from the Latin for "little ring"; occasionally annelation) is a chemical reaction in which a new ring is constructed on a molecule.[1]

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:[2]

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

Transannular interaction

A transannular interaction in chemistry is any chemical interaction (favorable or nonfavorable) between different non-bonding molecular groups in a large ring or macrocycle.[3] See for an example the molecule atrane.

References

  1. ↑ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "annulation". IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "annelation".
  2. ↑ Construction of Bicyclic Ring Systems via a Transannular SmI2-Mediated Ketone-Olefin Cyclization StrategyGary A. Molander, Barbara Czakó, and Michael Rheam J. Org. Chem.; 2007; 72(5) pp 1755 - 1764; (Article) doi:10.1021/jo062292d
  3. ↑ Experimental evidence in support of transannular interactions in diketones Kata Mlinaric-Majerski, Marijana Vinkovic, Danko Škare, Alan P. Marchand Arkivoc DS-339E 2002 Online Article
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