Rearrangement reaction
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A rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule [1] . Often a substituent moves from one atom to another atom in the same molecule. In the example below the substituent R moves from carbon atom 1 to carbon atom 2:
Intermolecular rearrangements also take place.
A rearrangement is not well represented by simple and discrete electron transfers (represented by curly arrows in organic chemistry texts). The actual mechanism of alkyl groups moving, as in Wagner-Meerwein rearrangement, probably involves transfer of the moving alkyl group fluidly along a bond, not ionic bond-breaking and forming. In pericyclic reactions, explanation by orbital interactions give a better picture than simple discrete electron transfers. It is, nevertheless, possible to draw the curly arrows for a sequence of discrete electron transfers that give the same result as a rearrangement reaction, although these are not necessarily realistic.
Some key rearrangement reactions:
Examples are the Wagner-Meerwein rearrangement:
and the Claisen rearrangement:
[edit] References
- ^ March, Jerry (1985). Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third Edition, John Wiley & Sons. ISBN 0-471-85472-7.
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