Rearrangements – Diastereoisomer 3

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

With the leaving group –N2+ axial the atom best placed to migrate is the green hydrogen. This hydrogen is anti-periplanar to the leaving group so it migrates.

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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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