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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P. Lewis, S. Middleton, M. Rosser and L. Stock, Aust. J. Chem., 1980, 33, 1049.

Z.-L. Song, C.-A. Fan and Y.-Q. Tu, Chem. Rev., 2011, 111, 7523–7556.

 

 

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