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One possible route for formation of 5 involves initial rearrangement of a 1,3-diisobutenyl-2,2,4,4-tetramethylcyclobutane radical cation to a 1,3-distonic radical cation with the radical center on a cyclopentane ring and the charge on the isopropyl group. Deprotonation of this radical cation gives a cyclopentyl radical that, after a methyl shift and addition of the subsequent radical center to the remaining isobutenyl group, generates the required bicyclo[3.1.0] ring system with an isopropyl radical at the 3-position. This radical can then be reduced to the anion which is protonated to give 5.
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