Conformational Analysis of Decalins | Cis Decalins & Trans Decalins | Stereochemistry

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In this video we will present the conformational analysis of decalins and bridge ring compounds.
Conformations
The infinite number of arrangements of the atoms or groups of a
molecule in three dimentional space which are interconvertible into
each other by rotation about single bond are called Conformations or Rotational Isomers or simply Rotamers. These conformers have different internal dimensions (atom-to-atom distances, dihedral angles, dipole moment etc.)
.
The energy barrier for rotation of carbon-carbon single bonds
(conversion of different spatial arrangements) is normally small, smaller than 0.6 kcal/mol and greater than 16 kcal/mol.
Compounds with two or more rings fused together
• Spirocyclic: -Two or more rings.
- Each pair of rings shares one common carbon atom.
• Bicyclic: Two rings that share two or more common atoms
Confromation of Decalin
(Decahydronaphthalene)
Fused Bicyclic system
Saturated analogue of naphthalene and can be prepared from it by hydrogenation in a fused state in the presence of a catalyst
Decalin is a hydrocarbon which has six-membered rings like those of cyclohexane, are expected to be most stable in the chair form. However, there are two possible ways in which two chairs conformations of cyclohexane can be joined.
Each chair is fused to the other by equatorial bonds, leaving the angular hydrogens (Ha) axial to both rings. The hydrogens on the ring junction carbons are trans in this diastereomer.
Chair conformations the rings are fused by one axial and one equatorial bond and the overall structure is bent at the ring fusion. (C-1 axial, C-6 equatorial) The hydrogens on the ring junction carbons are cis to each other.
Bridged Ring Compounds
In a bridged bicyclic compound , two rings share two carbon atoms and these carbon atoms are not adjacent.
Bicyclo Pentane
Bicyclo Heptane ( Norborane)
Bicyclo Octane
Propellanes & Admantane
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