Fragmentation – Fragmentations are controlled by stereochemistry (Trans isomer)

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

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In the cis isomer both substituents can be equatorial. However, in the trans isomer, one substituent has to be axial. This will mainly be the mesylate group, since the NH₂ group suffers greater 1,3-diaxial interactions.
^{Click the links below to view animations for both trans isomers:}

Severe interactions

Less severe interactions

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U. Burckhardt, C. A. Grob and H. R. Kiefer, Helv. Chim. Acta, 1967, 50, 231–244.