Fragmentation – Fragmentations are controlled by stereochemistry (Trans isomer – Less severe interactions)

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}

For the trans isomer, fragmentation of the most populated conformation is impossible because the leaving group is not anti-periplanar to any C-C bond. The only bonds anti-periplanar to the mesylate group are C-H bonds (at the 3 and 5 position), making this compound ideally set up for another reaction whose requirements for anti-periplanarity you have already met-E2 elimination.

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