The bridged bicyclic norbornane, formally bicyclo[2.2.1]heptaneThe spirocyclic compound spiro[5.5]undecaneDABCO (1,4-diazabicyclo[2.2.2]octane) is often incorrectly depicted with one skewed ethylene group for the sake of clarity.
A bicyclic molecule (from bi 'two', and cycle 'ring') is a molecule that features two joined rings.[1] Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (all of the ring atoms are carbons), or heterocyclic (the rings' atoms consist of at least two elements), like DABCO.[2] Moreover, the two rings can both be aliphatic (e.g. decalin and norbornane), or can be aromatic (e.g. naphthalene), or a combination of aliphatic and aromatic (e.g. tetralin).
Three modes of ring junction are possible for a bicyclic compound:[3]
In spiro compounds, the two rings share only one single atom, the spiro atom, which is usually a quaternary carbon.[4] An example of a spirocyclic compound is the photochromic switch spiropyran.
In fused/condensed[5]bicyclic compounds, two rings share two adjacent atoms. In other words, the rings share one covalent bond, i.e. the bridgehead atoms are directly connected (e.g. α-thujene and decalin).
In bridged bicyclic compounds, the two rings share three or more atoms, separating the two bridgehead atoms by a bridge containing at least one atom. For example, norbornane, also known as bicyclo[2.2.1]heptane, can be viewed as a pair of cyclopentane rings each sharing three of their five carbon atoms. Camphor is a more elaborate example.
C8, C9, and C11 bicyclic alkanes. The bridgehead atoms are the carbons from which three bonds radiate, like spokes:bicyclo[2.2.2]octane, bicyclo-[3.3.1]nonane, bicyclo[3.3.3]undecane.
^Smith, Michael B. (2011-06-29). Organic Chemistry: An Acid—Base Approach. CRC Press. ISBN 978-1-4200-7921-0.
A bicyclicmolecule (from bi 'two', and cycle 'ring') is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many...
segments, for example helicenes and acenes. In transannulation a bicyclicmolecule is created by intramolecular carbon-carbon bond formation in a large...
with conjugated double bonds. This unsaturated arrangement means the bicyclicmolecule is planar. Guanine, along with adenine and cytosine, is present in...
the shift of divalent group, as part of a three-membered ring, in a bicyclicmolecule. [3,3] sigmatropic shifts are well studied sigmatropic rearrangements...
expels a leaving group (a halide) forming a bicyclicmolecule with rings smaller than the original. The bicycle is then opened by nucleophilic attack on...
1.0]butane is an organic compound with the formula C4H6. It is a bicyclicmolecule consisting of two cis-fused cyclopropane rings, and is a colorless...
is maintained by direct transannular bonding to form a fused 7–5 bicyclicmolecule. Cyclodecatetraene is a stable, non-aromatic 8 π-electron system with...
Trithiapentalene is an organic bicyclicmolecule containing two sulfur heterocycles. Its 10-π aromatic structure is similar to naphthalene. There has...
Ice Choir from the 2012 album Afar a type of ring binder Bicyclicmolecule, two-ringed molecule Heterocyclic compounds, 2-ring Two Ring Circus (disambiguation)...
Chemical Society 1981 103 (6), 1372-1375 doi:10.1021/ja00396a013 Unusual bicyclicmolecule extends frontier of aromaticity Katrina Krämer Chemistry World 2017...
synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclicmolecule, but the reactants used in its preparation are fairly simple: succinaldehyde...
tetrahydroxytetraborate ion ([B4O5(OH)4]2−). This anion is a bridged bicyclicmolecule, contains oxygen atoms bridging the boron atoms, which are linked...
original on 2016-08-19. Retrieved February 21, 2023. "'Olympic rings' molecule olympicene in striking image". BBC Online. 27 May 2012. Retrieved 28 May...
Vince lactam is the commercial name given to the bicyclicmolecule γ-lactam 2-azabicyclo[2.2.1]hept-5-en-3-one. This lactam is a versatile chemical intermediate...
the 1,4- position, and is a bridged bicyclic compound. The compound is a prototype of a class of strained bicyclic hydrocarbons. The compound was originally...
cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, and so on. Bicyclic alkanes include bicycloundecane, decalin, and housane. Polycyclic alkanes...
ring appears in a single molecule. Naphthalene is formally a polycyclic compound, but is more specifically named as a bicyclic compound. Several examples...
Benzoxepin is an oxygen-containing bicyclicmolecule consisting of an oxepin ring and a benzene ring. There are three isomers, varying in where the oxygen...
heterocycles. Part III. Aromaticity of 1,3-imidazole in 5+n hetero-bicyclicmolecules". Journal of Molecular Structure. 655 (3): 397–403. Bibcode:2003JMoSt...
effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases...
(decahydronaphthalene, also known as bicyclo[4.4.0]decane and sometimes decaline), a bicyclic organic compound, is an industrial solvent. A colorless liquid with an...
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