Rearrangements – Diastereoisomer 4

NOTE: Important charges and non-bonding electrons are shown throughout the animation except during the transition phase

^{Click the structures and reaction arrows in sequence to view the 3D models and animations respectively}

The hydroxyl group is ideally positioned to displace N₂ and form an epoxide, as both groups are axial and anti-periplanar. This is an example of neighbouring group participation.

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