Iodoheptene Radical Cyclisation Exo

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

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The reaction proceeds via an abstraction of iodine by a trimethyltin radical. The chain can then twist into a position to cyclise and form the major exo product. The abstraction of hydrogen from trimethyltinhydride by the methylcyclohexane radical to form the exo product is not shown.

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H. Fischer and L. Radom, Angew. Chemie Int. Ed., 2001, 40, 1340–1371.