Cyclopentenyl systems, solvolysis

Cyclopentadienyl iodide (5-iodo-l,3-cyclopentadiene) reacts approximately 10 times as rapidly as cyclopentenyl iodide (3-iodocyclopentene) with tetrabutylammonium bromide under the same conditions (Breslow, R. Canary, J. W., J. Am. Chem. Soc., 1991, 113, 3950). Under solvolysis conditions (SnI), the reactivity order is reversed. Provide a rationalization based on the frontier orbitals of the system. What would you predict for the analogous 3- and 7-membered ring systems ... 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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