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Tutorial MenuePericyclic ReactionsLearning Unit 5 of 6

Pericyclic Reactions: Sigmatropic Rearrangements

Sigmatropic Rearrangments: Examples for [n,m] Sigmatropic 10-Electron Systems

10-Electron systems

The [5,5] sigmatropic rearrangement of 2,4-pentadienylphenyl ethers can be considered a homologous Claisen rearrangement.

[5,5] Sigmatropic rearrangement

The major reaction is a Claisen rearrangement ([3,3] sigmatropic). In addition, formation of the para-substituted aromatic compound by a [5,5] sigmatropic rearrangement is being observed. A [3,5] sigmatropic rearrangement does not take place because, as a reaction with 8 electrons, it is suprafacially forbidden. The benzidine rearrangement represents another example of a [5,5] sigmatropic reaction.

Benzidine rearrangement
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