Inorganic chemistry, analicyclic compound contains one or more all-carbonrings which may be eithersaturated or unsaturated, but do not havearomatic character.[1] Alicyclic compounds may have one or morealiphaticside chains attached.
The simplest alicyclic compounds are the monocycliccycloalkanes:cyclopropane,cyclobutane,cyclopentane,cyclohexane,cycloheptane,cyclooctane, and so on.Bicyclic alkanes includebicycloundecane,decalin, andhousane.Polycyclic alkanes includecubane,basketane, andtetrahedrane.
Spiro compounds have two or more rings that are connected through only one carbon atom.
The mode of ring-closing in the formation of many alicyclic compounds can be predicted byBaldwin's rules.
Otto Wallach, a German chemist, received the 1910Nobel Prize in Chemistry for his work on alicyclic compounds.[2][3]
Cycloalkenes
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Monocycliccycloalkenes arecyclopropene,cyclobutene,cyclopentene,cyclohexene,cycloheptene,cyclooctene, and so on. Bicyclic alkenes includenorbornene andnorbornadiene.
Two more examples are shown below,methylenecyclohexane on the left and1-methylcyclohexene on the right:
Right: regular double bond
Anexocyclic group is always shown outside the ring structure, take for instance the exocyclic double bond of the former molecule.Isotoluenes are a prominent class of compounds with exocyclic double bonds.
The placement of double bonds in many alicyclic compounds can be predicted withBredt's rule.
References
edit- ^IUPAC,Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (1995) "Alicyclic compounds".doi:10.1351/goldbook.A00216
- ^Leopold Ruzicka (1932). "Third Pedler lecture. The life and work of Otto Wallach".J. Chem. Soc.: 1582.doi:10.1039/JR9320001582.
- ^Christmann, M (2010). "Otto Wallach: Founder of Terpene Chemistry and Nobel Laureate 1910".Angewandte Chemie International Edition.49 (50):9580–9586.doi:10.1002/anie.201003155.PMID 21110354.